C2-Allens Made Chemistry Exercise {PART-2}

1 6 . The final product obtained in the reaction is : H3C OCH3 + HBr (A) CH3 OH (B) CH3 Br (C) CH3 O CH3 (D) None of these 1 7 . The acidity of the compounds RCOOH, H2CO3, C6H5OH, ROH decreases in the order : (A) RCOOH > H2CO3 > C6H5OH > ROH (B) C6H5OH > RCOOH > H2CO3 > ROH (C) ROH > C6H5OH > RCOOH > H2CO3 (D) H2CO3 > RCOOH > C6H5OH > ROH 1 8 . Arrange the following in order of decreasing acidic strength. p- nitrophenol (I), p-cresol (II), m-cresol (III), phenol (IV) : (A) I > II > III > IV (B) IV > III > II > I (C) I > III > II > IV (D) III > II > I > IV 1 9 . For the cleavage of ethers by halogen acids, the order of reactivity of halogen acids is : (A) HI > HBr > HCl (B) HBr > HI > HCl (C) HCl > HBr > HI (D) Ethers do not undergo cleavage 2 0 . Consider the following reactions : dil.KMnO4 A (CH3COO)4Pb B Cold The product (B) is OH CH3COO O O (A) (B) (C) (D) OH CH3COO O O 2 1 . The major product (A) formed in the reaction H2SO4 A HO OH is : (A) (B) (C) (D) O OO

2 2 . In the reaction Cl CH3Br + CH3CHO + Mg Dry ether A H3O+ B the product (B) is : (A) CH3CH CH2Br (B) Cl CH2CHCH3 OH OH (C) CH3–CH CH2CHCH3 (D) CH2=CH CH2Br OH OH 2 3 . The products formed in the reaction are : O C6H5 C 18 H2SO4 Heat OH + CH3OH O O 18 18 (A) C6H5 C OCH3 and H2O (B) C6H5 C OCH3 and H2O O 18 18 (D) C6H5OCH3, CO and H2O (C) C6H5 C CH2OH and H2O 2 4 . The conversion O OH CH3 C CH2CH2CO2CH3 CH3 CH CH2CH2CO2CH3 (A) LiAlH4 and then H+ (B) NaBH4 and then H+ (D) None of these (C) H2/ Carbon 2 5 . Identify the final product of the reaction : CH3MgBr + CH2CH2 H3O+ ? O (A) CH3OH (B) CH3CH2OH (C) (D) CH3CH2CH2OH CHECK YOUR GRASP ANSWER KEY EXERCISE -1 Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Ans. C B C C A C C D B B C D C A C A A A A C Que. 21 22 23 24 25 Ans. A B A B D

EXERCISE–02 BRAIN TEASERS SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS) 1 . Consider the following reaction. Br (B) (1S,3R)-cis-3-methylcyclohexanol + KOH H2O (D) (1R,3R)-trans-3-methylcyclohexanol SN 2 H H CH3 (1R, 3S)-cis-1 -Bromo -3-methylcyclohexane The product formed in the reaction is (A) (1R, 3S)-cis-3- methylcyclohexanol (C) (1S, 3S)-trans-3-methylcyclohexanol 2 . Consider the following alcohols CH2OH CH2OH CH2OH CH2OH O2N CH3O Br (I) (II) (III) (IV) The order of decreasing reactivities of these alcohols towards nucleophilic substitution with HBr is (A) III > I > IV > II (B) III > I > II > IV (C) I > III > IV > II (D) I > III > II > IV 3 . The product formed in the following reaction O COOC2H5 NaBH4  is H 2 O ,C H 3 O H O CH2OH HO CH2OH HO COOC2H5 COOC2H5 (A) (D) (B) (C) 4 . Consider the following sequence of reactions. C H C  CH CH3MgBr  A 1.HCHO B 25 2 .H 3 O  The product (B) is (A) CH CH OH (B) C 2 H 5 C  CHCH2OH 32 | CH3 (C) C2H5C  C – CH – CH3 (D) CHC  C – CH OH | 25 2 OH 5 . In the transformations PhCH = CH ArCO3H A 1.LiAlH4 ,Et2O B 2 CH2Cl2 2.H2O the end product (B) is (A) PhCH—CH2 (B) PhCHOH CH (C) PhCH CH COAr (D) PhCH CH OH O 3 22 22

6 . The reactivities of methanol (1), 1- propanol (II), 2- butanol (III) and 2- methyl-2- propanol (IV) towards sodium metal follow the order (A) I > II > III > IV (B) IV > III > II > I (C) I > IV > II > III (D) IV > II > III > I 7 . In the reaction (CH ) C–O–CH CH + HI heat  33 23 (1 mole) the product(s) formed is (are) (B) (CH3)3C–I and CH3CH2OH (A) (CH3)3 C–OH and CH3CH2I  3I (C) (CH ) C–I and CH CH I (D) (CH 3 )3 C O  CH2CH 33 3 2 | H 8 . Consider the following sequence of reactions. OH 1. KH  A 1. B2H6 B 2. PhCH2Br 2. H2O2 / OH The end product (B) is (A) O Ph (B) HO O Ph OH (D) Ph OH (C) O Ph 9 . In the reaction CH3 + HCl  HO the major product formed is Cl OH OH Cl (A) (B) Cl Cl (D) Cl (B) (B) CH3O14CH2–CH–CH2 1 0 . Consider the following reaction. O 14CH2–CH–CH2Cl CH3O  A 14 O (D) CH3OCH2–CH–CH2OCH3 The product (A) is OH (A) 14CH2–CH–CH2OCH3 O 14 (C) HO–CH2–CH–CH2OCH3 OCH3

CH3 11. In the reaction C–CH2 H2O18  A , the product (A) has the structure : CH3 O H CH3 CH3 CH3 CH3 (A) CH3–C–CH2OH (B) CH3–C–CH218OH (C) CH3–C–CH3 (D) CH3–CH–CH218OH 18OH OH 18OH 1 2 . The compound which does not react with sodium is (A) CH3CHOHCH3 (B) CH3OCH3 (C) CH3COOH (D) CH3CH2OH 1 3 . Which of the following ethers is not cleaved by concentrated HI even at 525 K ? OCH3 O (A) (B) OCH2CH2CH3 (D) (C) O OH 1 4 . Which of the following reactions can be used to prepare CH3– C – C6H5 O C2H5 (A) CH3– C – C6H5 + C H MgBr [ ] H3O+ 25 O (B) C2H5 – C – C6H5+ CH MgBr [ ] H3O+ 3 O (C) CH3– C – C2H5 + C H MgBr [ ] H3O+ 65 Br Alc.KOH (D) CH3– C – C6H5  C2H5 1 5 . What are the products expected in the following reactions ? OO CH2N2 C6H5 – C – CH2– C – CH3 Ether OCH3 O O OCH3 (A) C6H5C = CH – C – CH3 (B) C6H5C – CH = C – CH3 OCH3 O O OCH3 (C) C6H5– C – CH – C – CH3 (D) C6H5– C – CH – C – CH3 CH2 CH2

1 6 . Which of the following groups will increase the acidity of phenol? (A) – NO2 (B) –CN (C) –X (halogen) (D) None of these 1 7 . In the esterification of propanoic acid with methanol in the presence of a mineral acid, which of the following are intermediate species? OH OH OH OH (D) C2H5– C – OCH3 (A) C2H5– C – OH (B) C2H5– C – OH (C) C2H5– C – OH OCH3 1 8 . The intermediate stages in the conversion (CH3)2– C – C – (CH3)2 dil.H2SO4 CH COC (CH ) are OH OH  3 33 (A) (CH3)2– C – C(CH3)2 (B) (CH3)2– C – C(CH3)2 OH OH2 OH (C) CH3– C – C(CH3)3 (D) CH3– C – C(CH3)3 OH OH 1 9 . An alcohol, on treatment with P + I followed by the reaction of the formed product first with AgNO and 22 then with HNO and final basicification, gives a blue colour. Which of the following alcohols can it be? 2 (A) CH CH OH (B) (CH ) CHOH 32 32 (C) (CH ) C – OH CH3 CHOH 33 (D) C2H5 2 0 . Which of the following will result in the formation of an ether? – – (A) (CH3 )3 C ON a + CH CH Br (B) (CH ) CBr + C2H5 ON a 32 33 – (C) C H ONa + CH Br (D) C H Br + CH3 ON a 65 3 65 BRAIN TEASERS ANSWER KEY EXERCISE -2 10 11 12 13 14 15 Que. 1 2 3 4 5 6789 B A B B A,B,C A,B D B ABBB Ans. C A C 19 20 B,D A ,C Que. 16 17 18 An s . A,B,C A,B,C,D A,B,C,D

EXERCISE–03 MISCELLANEOUS TYPE QUESTIONS TRUE OR FALSE : 1 . Lower alcohols are more soluble in water than higher alcohols. 2 . Tertiary alcohols are more reactive towards halogen acids than secondary alcohols. 3 . Glycerine is more viscous than ethylene glycol. 4 . Tertiary alcohols are more acidic than phenol. 5 . Phenol on heating with CCl4 in presence of NaOH at 340 K followed by acetylation gives aspirin. 6 . Phenol does not decompose NaHCO3 to evolve CO2 but picric acid does. 7 . m-Methoxyphenol is a weaker acid than phenol. 8 . Sodium ethoxide is prepared by the reaction of ethanol with aqueous sodium hydroxide. FILL IN THE BLANKS : 1 . Lower alcohols are highly soluble in water due to ........................ 2 . The reaction of phenol with a diazonium salt in weak alkaline medium is called........................ 3 . Absolute alcohol can be prepared from rectified spirit by ........................ distillation. 4 . A mixture of phenol and phthalic anhydride when heated with conc. H2SO4 forms ........................which is used as an ........................in acid-base titrations. 5 . Tertiary alcohols when passed over heated copper undergo ........................to form........................ 6 . One mole of glycerol when heated with two moles of HIO4 gives two moles of ........................and one mole of ........................ 7 . The acidity of phenol is due to the ........................of its anion. 8 . A........................ diol has two hydroxyl groups on........................ 9 . Phenol is acidic because of resonance stabilization of its conjugate base, namely........................ 1 0 . Amongst the three isomers of nitrophenols, the one that is least soluble in water is........................ MATCH THE COLUMN 1 . Match the column I with column II. Column-II (Possible products) Column-I (Reaction) (i) Hg(OAc)2/H2O ( A ) —CH3 (ii) NaBH4 ( p ) —CH2OH (i) B2H6/THF OH (B) CH2 (ii)H2O2 OH (q) —CH3 ( C ) —CH3 H/H2O OH ( r ) —CH3 (i) Hg(OAc)2/H2O OH ( D ) —CH3 (ii) NaBH4 —CH3 (s)

2 . Match the column I with column II. Column-II Column-I (Product) (substrate + RMgX) ( p ) Tertiary alcohol (A) HCHO ( q ) First ketone then 3° alcohol O (B) CH3—C—CH3 ( C ) CH3—CH—CH—CH3 ( r ) Secondary alcohol O ( s ) Primary alcohol ( D ) Ester ASSERTION & REASON QUESTION : These questions contains, Statement-I (assertion) and Statement-II (reason). (A) Statement-I is True, Statement-II is True ; Statement-II is a correct explanation for Statement-I (B) Statement-I is True, Statement-II is True ; Statement-II is NOT a correct explanation for Statement-I (C) Statement-I is True, Statement-II is False. (D) Statement-I is False, Statement-II is True. 1 . Statement-I : Solubility on n-alcohols in water decreases with increase in molecular weight. Because Statement-II : The relative proportion of the hydrocarbon part in alcohols increases with increasing molecular weight which permits enhanced hydrogen bond with water. 2 . Statement-I : p- Nitrophenol is a stronger acid than o-nitrophenol. Because Statement-II : Intramolecular H-bond makes o-isomer weaker than p-isomer. 3 . Statement-I : Phenol is more reactive than benzene towards Because Statement-II : In the case of phenol, the intermediate carbocation is more resonance stabilized. 4 . Statement-I : Tert-Butoxide is a stronger base than OH– or C2H5O– ion but is a much poorer nucleophile. Because Statement-II : A negatively charged ions is always more powerful nucleophile than its conjugate acid. 5 . Statement-I With Br2–H2O, phenol gives 2,4,6- tribromophenol but with Br-CS2, it gives 4-bromophenol as the major product. Because Statement-II : In water ionization of phenol is enhanced but in CS2, it is greatly suppressed. COMPREHENSION BASED QUESTIONS : Comprehension # 1 Phenols are converted into their salts by aqueous NaOH but not by aqueous bicarbonates. The salts are converted into the free phenols by aqueous mineral acids, carboxylic acid or carbonic acids. Most phenols have Ka value of about 10–10, and are tremondously more acidic than alcohols. The difference in acidity are

due to difference in stabilities of reactants and products. Phenol and phenoxide ions contain benzene ring and therefore must be hybrid of Kekuley structures OH OH O O and Being basic, oxygen can share more than a pair of electron with the ring. +O–H +O–H +O–H O O O and Phenol Phenoxide ion Since energy must be supplied to separate opposite charge, the structure of phenols should contain more energy. The net effect of resonance is therefore to stabilise the phenoxide ion to a greater extent than the phenol and thus to shift the equilibrium towards ionization and make Ka larger than for an alcohol. 1 . Which of the following is strongest acid ? OH (A) H2CO3 (B) (C) CH3–OH (D) CH3–CH2–OH 2 . Consider the following curves : Potential Energy A (A) Curve A represents the ionisation of alcohol B (B) Curve B represent the ionisation of Phenols (C) Curve A represents the ionisation of phenol Progress of reaction (D) None 3 . Which of the following is more stable: +OH O (A) (B) (C) Both (D) Unpredictable 4 . Correct order of acidity is OH OH OH OH (B) NO2 > > CH3 (A) H2CO3 > CH3–OH > NO2 OH (C) H2CO3 > > CH3 – OH (D) Both B and C

5 Choose the correct statement: (A) Phenol gives effervescence with NaHCO3 (B) Picric acid is weaker acid than carbonic acid O (C) Picric acid gives effervescence with NaHCO3 (D) R–O is more stable than Comprehension # 2 Symmetrically substituted epoxides give the same products in both the acid catalysed and base catalyzed ring opening. An unsymmetrical epoxide gives different products under acid catalysed and base catalysed conditions. Under basic conditions, the alkoxide ion simply attacks the less hindered carbon atom in an SN2 displacement. Under acidic conditions, the alcohol, attacks the protonated epoxide. HHH O O O CH2– C – CH3 + + CH3 CH2– C – CH3 CH2– C – CH3 (I) CH3 CH3 (II) (III) Structure II and III show that the oxirane carbon share part of positive charge. The tertiary carbon bear a larger part of positive charge and it is more strongly electrophilic. The bond between tertiary carbon and oxygen is weaker implying a lower transition state energy for attack at the tertiary carbon. Attack by the weak nucleophilic is sensitive to the strength of electrophilic is sensitive to the strength of electrophile. Centre attack takes place at more electrophilic carbon which is usually the more substituted carbon because it can better support the positive charge. 1 . What will be the products in following reactions O CH3– CH2ONa X CH3 CH3– CH2OH OH H (B) OCH2CH3 (C) H CH3 (A) OCH2–CH3 CH3 H (D) (C) CH3 CH3 C2H5 (D) None O H2SO4 Y 2 . CH3– CH2–OH CH2–CH3 C2H5 (B) C2H5 (A)

O18 H2O/H+ Z 3. CH2 CH CH3 (A) CH2 CH (B) CH2 CH (C) CH2 CH (D) None CH3 CH3 CH3 OH O (D) 4. CH3–ONa P: CH3–OH OH OCH3 (A) OCH3 (B) OH (C) 5. H2SO4 Q: (A) CH3–OH (B) (C) (D) None Comprehension # 3 When pinacol is treated with dilute H2SO4, a re-arrangement reaction takes place which leads to the formation of a ketone. OH OH O CH3 CH3 C C CH3 H2SO4 CH3 C C CH3 CH3 CH3 CH3 This reaction involves re-arrangement of carbocation. Step 1: •• •• + OH OH OH OH OH2 + CH3 C C CH3 H+ CH3 C C CH3 CH3 CC CH3 CH3 CH3 CH3 CH3 CH3 CH3

Step 2 : Carbocation rearrange by hydride, alkyl or aryl shift to get as stable as they can. Stability is the driving force for re-arrangement migration of bond may also occur. Where by ring expansion and ring contraction takes place. The relief of strain can provide a powerful driving force for re-arrangement. OH •••• + OH CH3 CH3 CC CH3 1,2-shift CH3 C C CH3 + CH3 CH3 CH3 +O–HCH3 O CH3 CH3 C C CH3 –H CH3 C C CH3 CH3 CH3 CH3 1 . What will be the product of following reaction CH3 C CH2 Br NaOH P, P is : CH3 (A) CH3 C CH CH3 (B) CH3 CH CH CH2 CH3 CH3 (C) Both of these (D) None of these 2 . What will be the product of following reaction CH3 OH OH Q H2SO4 C C CH3 Q is : (A) CH3 C CH2 CH3 (B) CH3 C CH CH3 OH (C) Both (D) None 3 . What will be the product of following reaction H2SO4 R is : (A) (B) (C) Both (D) None

4 . What will be the product of following reaction CH3 S is : OH H+ S, CH3 OH O (A) C–CH3 (B) (C) Both (D) None CH3 O CH3 5 . What will be the product of following reaction OH OH H ? CH—CH  O O (A) C—CH2 (B) C (C) both (D) None MISCELLANEOUS TYPE QUESTION ANSWER KEY EXERCISE -3  True / False 4. F 5. T 1. T 2. T 3. T 6. T 7. T 8. T  Fill in the Blanks 1. H-bonding 2. coupling reaction 3. azeotropic 4. phenolphthalein, indicator 7. resonance stabilisation 5. dehydriation, alkene 6. formaldehyde, formic acid 10. O-nitrophenol 8. vicinal, adjacent 9. phenoside ion  Match the Column 1. (A) q ; B p ; (C)  r ; (D) q 2. (A) s ; (B) p ; (C)  r ; (D) q  Assertion - Reason Questions 1. C 2. A 3. A 4. B 5. A  Comprehension Based Questions Comprehension #1 : 1. (A) 2. (B) 3. (B) 4. (D) 5. (C) Comprehension #2 : 1. (A) 2. (A) 3. (B) 4. (A) 5. (B) Comprehension #3 : 1. (A) 2. (A) 3. (B) 4. (A) 5. (B)

EXERCISE–04 [A] CONCEPTUAL SUBJECTIVE EXERCISE 1 . C2H5OH PCl5  (A) KCN (B) H3O  (C) NH3 (D) heat  (E) 2 . CH3CH2CH2OH PBr5  (A) KOH(Alc.) (B) HBr (C) NH3 (D) 3 . t-butyl alcohol reacts less rapidly with metallic sodium than the primary alcohol. Explain why? 4 . Explain why ArOR ethers are cleaved to give RI and ArOH rather than ArI and ROH. 5 . Complete tthe following reactions : CH3 H3C O (b) C H 3M gB r  (a) SOCl2  OH H3C H2O 6 . Complete tthe follofing reactions : Ph (b) OsO4  (a) O HI NaHSO3 Hg(OAc)2  NaBH4  7 . Provide products in the following reactions : CH3OH (a) OH SOCl2  (b) Pyridine (c) mCPBA 8 . Identify the products A and B giving proper explanation : CH3 CH3 CH3C––CH2 + H2O18 H A, CH3C––CH2 + CH3OH CH3ONa  B O O 9 . Indicate bonds which are cleaved I : in basic conditions II : in acidic conditions CH3 H3C––C––CH2 aOb 1 0 . In the following SN2 reaction Me HI OH  (A) is .............. C6H5 SN 2 ( stereoisomer ) (dextro)

CONCEPTUAL SUBJECTIVE EXERCISE ANSWER KEY EXERCISE -4(A) 1 . (A) C H Cl; (B) C H CN; (C) C H COOH; (D) C H COONH ; 25 25 25 25 4 (E) C2H5CONH2 2 (A) C3H7Br; (B) CH3CH=CH2; (C) CH3CHBrCH3; (D) CH3CHNH2CH3 3 . The +I.E. of three methyl groups on central C-atom of tert-butyl alcohol makes is partially negative with the result that it pushes the electron pair of –OH bond towards H-atom and thus H-atom is not replaced easily. 4 . SN2 attack on a carbon of benzene ring does not occur nor does the high energy C6H5+ form by an SN1 reaction. Hence ArI cannot be a product even in an excess of conc. HI. 5 . (a) CH3 OH Cl (b) CH3––C––CH2CH3 CH3 6. (a) Ph OH 7 . (a) OH I (b) OH Cl (b) OCH3 H O CH3 (c) H H CH3 CH3 CH3 8 . CH3C––CH2 H+ CH3C––CH2 H2O18  CH3C––CH2(A) O O 18OH OH H (nucleophile attacks the more substituted carbon in acid-catalysed reaction) CH3  CH3 H CH3 CH3C––CH2 CH3O Na CH3C––CH2 (CH3OH) CH3C––CH2 O O OCH3 OH OCH3 (nucleophile attacks the less substituted carbon in base-catalysed reaction) 9 . I : bond b ; II : bond a 1 0 . A is laevo - isomer

EXERCISE–04 [B] BRAIN STORMING SUBJECTIVE EXERCISE 1 . A compound (X) reacts with thionyl chloride to give a compound (Y). (Y) reacts with Mg to form a Grignard reagent, which is treated with acetone and the product is hydrolysed to give 2-methyl-2- butanol. What are structural formulae of (X) and (Y) ? 2 . Compound (A) C4H10O reacts rapidly with metallic sodium, but undergoes almost no reaction with Lucas reagent. When (A) is treated with hot concentrated sulphuric acid, a new compound (B) C4H8 is formed. If C4H8 is hydrated with sulphuric acid a new compound (C) C4H9OH is formed, which is almost inert to metallic sodium but reacts rapidly with Lucas reagent. What are (A), (B) and (C) ? 3 . Give the product of the reaction of Ph2CHCH2OH with HBr and explain its formation. 4 . Hydration of 3-phenyl-1-butene in dilute H2SO4 is not a satisfactory method for preparing 3-phenyl-2- butanol, because 2-phenyl-2-butanol is obtained instead. Explain. 5 . When A (given below) reacts with HI products is B and not C. Explain. HI  HI O I OH OH I (C) (A) (B) 6 . Isotopic carbon-14 in (A) appears at new position (as in B) when (A) reacts with CH3ONa. Explain. 14 14CH2––CHCH2Cl + CH3ONa  CH3OCH2CH––CH2 O O (A) (B) 7 . Complete the following reaction CH2=CH2 1. HBr A H2O C 2. Mg C6H5CO3H B 8 . Complete the following reactions (a) CH3MgBr  A O H3O H3C CH2CH2CH3 CH3MgBr  A (b) H3O O H3C (c) CH3CH=CH2 mCPBA A C2H5MgBr  B H3O

9 . In the following dehydration of diol with H3PO4, following product is formed such that isotopic 18O goes with H2O. Explain. 18 OH O OH 9 H 3PO4 + H2O18 12 57 10 4 68 3 1 0 . In the following SN1 reaction : Me H Br O H  (A) is .............. SN1 ( stereoisomer ) Et (dextro)

BRAIN STORMING SUBJECTIVE EXERCISE ANSWER KEY EXERCISE -4(B) 1 . C2H5OH C2H5Cl Ethyl alcohol Ethyl chloride (X) (Y) 2 . (CH3)2CHCH2OH; (CH3)2C=CH2; (CH3)3COH (A) (B) (C) Ph 3 . Ph––C––CH3 Br Synchronous migration of Ph provides greater assistance in the removal of H2O form the protonated alcohol than does a methyl group. 4. H2C=CH–CH–CH3 H  + ~:H + H3C–CH–CH–CH3 H3C–CH2–C–CH3 Ph Ph Ph OH H2O  CH3CH2––C––CH3 H Ph (Hydration gives an intermediate 2°C+, which undergoes a hydride shift Although phenyl is a better migrator than H, migration of H occurs leading to a more stable 3° benzylic carbocation.) 5 . Bond energy of C (vinylic)––O bond () is greater than that of C(alkylic)––O bond (). Hence, when A reacts with HI, bond  breaks forming B. HI  I  B O O H 6 . CH3O– (nucleophile) attacks less submituted carbon (which is C-14 in this case) forming intermediate (C). 14 14 CH3O CH2––CHCH2Cl  CH3OCH2––CHCH2Cl OO (A) (C) (C) will displace Cl– forming (B) 14  14 CH3OCH2CH––CH2––Cl CH3OCH2CH––CH2 O O (C)

7. CH2––CH2 C 6 H5 CO 3 H CH =CH 1. HBr CH3CH2MgBr 2 2 2. Mg O (B) (A) A + B H2O CH3CH2CH2CH2OH (C) 8 . (A) (B) (C) CH3CH––CH2 HO O CH3 OH 9 . 3° alcohol at C is more basic than 2° alcohol at C . Hence, intramolecular dehydration takes place such 25 that H of 2° alcoholic group at C eliminates OH of 3° alcoholic groups at C (with isotopic 18O) to form 52 cyclic ether 18 OH O OH 5  + H2O18 2 1 0 . A is a mixture of d- and 1- and thus racemic mixture.

EXERCISE–05 PREVIOUS YEARS QUESTIONS 1 . The products of combustion of an aliphatic thiol (RSH) at 298 K are - [IIT-92] (A) CO2 (), H2O (g) and SO2 (g) (B) CO2 (g), H2O (g) and SO2 (g) (C) CO2 (), H2O () and SO2 (g) (D) CO2 (g), H2O () and SO2 () 2 . An organic compound C3H6O does not give a precipitate with 2, 4-dinitrophenyl hydrazine reagent and does not react with sodium metal. It could be - [IIT-93] (A) CH3 – CH2 – CHO (B) CH3 – CO – CH3 (C) CH2 = CH – CH2OH (D) CH2 = CH – OCH3 3 . When phenol is reacted with CHCl3 and NaOH followed by acidification, salicylaldehyde is obtained which of the following species are involved in the above mentioned reaction as intermediates ? [IIT-95] O OH O O H H CHCl2 CHCl2 (A) CCl2 (B) (C) CHCl2 (D) OH 4 . The reaction products of, C6H5OCH3 + HI   are : [IIT-95] (A) C6H5OH + CH3I (B) C6H5I + CH3OH (C) C6H5CH3 + HOI (D) C6H6 + CH3 OI 5 . The order of reactivity of the following alcohols - [IIT-97] CH3 CH3 CH3 CH3 Ph OH F OH OH F OH (I) (II) (III) (IV) towards conc. HCl is - (A) I > II > III > IV (B) I > III > II > IV (C) IV > III > II > I (D) IV > III > I > II 6 . Among the following compounds, the strongest acid is - [IIT-98] (A) HC  CH (B) C6H6 (C) C2H6 (D) CH3OH 7 . Benzenediazonium chloride on reaction with phenol in weakly basic medium gives - [IIT-98] (A) Diphenyl ether (B) p-hydroxyazobenzene (C) Chlorobenzene (D) Benzene 8 . The ether O – CH2 when treated with HI produces [IIT-99] (A) CH2I (B) CH2OH (C) I (D) OH [IIT-2000] 9 . Which one of the following will most readily be dehydrated in acidic condition - O OH OH O O (A) (B) (C) (D) OH OH

1 0 . 1-propanol & 2-propanal can be best distinguished by - [IIT-01] (A) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution (B) Oxidation with acidic dichromate followed by reaction with Fehling solution (C) Oxidation by heating with copper followed by reaction with fehling solution (D) Oxidation with concentrated H2SO4 followed by reaction with Feheling [IIT-02] 1 1 . Identify the corect order of boiling point of the following compounds - (A) CH3CH2CH2CH2OH ; (B) CH3CH2CH2CHO ; (C) CH3CH2CH2COOH (A) A > B > C (B) C > A > B (C) A > C > B (D) C > B > A 12. OH + C2H5I C2H5O¯Na  (excess )  [IIT-03] C2H5OH (anhydrous ) (A) OC2H5 (B) I (C) C6H5OC6H5 (D) C2H5OC2H5 1 3 . Reaction of entainomerically pure acid with 1 chiral carbon and racemic alcohol with 1 chiral carbon gives an ester which is : [IIT-03] (A) Meso (B) Optically active (C) Racemic mixture (D) Enantionmerically pure 1 4 . CH3MgBr + Ethyl ester  which can be formed as product (excess) : [IIT-03] CH2CH3 CH3 (A) HO CH2CH3 (B) HO CH2CH2CH3 CH2CH3 CH2CH3 CH2CH3 CH3 (C) HO CH2CH3 (D) HO CH3 CH3 CH3 1 5 . On acid catalysed hydration, 2-phenyl propene gives : [IIT-04] (A) 3-phenyl-2-propanol (B) 2-phenyl-1-propanol (C) 1-phenyl-3-propanol (D) 2-phenyl-2-propanol 1 6 . Conversion of cyclohexanol into cyclohexene is most effective in : [IIT-05] (A) concentrated H3PO4 (B) concentraated HCl (C) concentrated HCl / ZnCl2 (D) concentrated HBr 1 7 . When t-butanol and n-butanol are separately treated with a few drops of dilute KMnO in one case only, 4 purple colour disappears and a brown precipitate is formed. Which of the two alcohols gives the above reaction and what is the brown precipitate ? [IIT-94] 1 8 . 3,3-Dimethylbutan-2-ol loses a molecule of water in the presence of a concentrated sulphuric acid to give tetramethyl ethylene as a major product. Suggest a suitable mechanism. [IIT-96] 1 9 . A compound D(C H O) upon treatment with alkaline solution of iodine gives a yellow precipitate. The 8 10 filtrate on acidification gives a white solid (E) (C H O ). Write the structures of (D) and (E) and explain the 762 formation of (E). [IIT-96]

2 0 . Which of the following is the correct method for synthesising methyl-t-butyl ether and why? (i) (CH ) CBr + NaOMe  (ii) CH Br + tert-BuONa  [IIT- 97] 33 3 O C OH HOCH2 Conc.H2SO4 (A) 21. + [IIT-97] O C OH HOCH2 2 2 . Write the intermediate steps for the following reaction: [IIT- 98] (i) H OH O CH3 2 3 . Discuss why o-hydroxy benzaldehyde is a liquid at room temperature while p-hydroxy benzaldehyde is a high melting solid? [IIT-99] 2 4 . Write the structures of the product A & B + [IIT-2000] CH3 C O18C2H5 H3O A + B O 2 5 . Cyclobutyl bromide on treatment with magnesium in dry ether forms an organometallic A. The organometallic reacts with ethanal to give an alcohol B after mild acidification. Prolonged treatment of alcohol B with an equivalent amount of HBr gives 1- bromo-1-methylcyclopentane (C). Write the structures of A, B and explain how C is obtained from B. [IIT-2001] 2 6 . How would you synthesis 4- methoxyphenol from bromobenzene in NOT more than five steps? State clearly the reagents used in each step and show the structures of the intermediate compounds in your synthetic scheme. [IIT-2001] 2 7 . Identify X, Y and Z in the following synthetic scheme and write their structure. Explain the formationof labelled formaldehyde (H C*O) as one of the products when compound Z is treated with HBr and subsequently 2 ozonolysed. Mark the C* carbon in the entire scheme. BaC*O + H SO   X (gas) [C* denotes C14] 3 24 CH = CH – Br (i ) Mg / ether Y LiAlH4  Z [IIT-2001] 2 ( ii ) X, ( iii )H3O 2 8 . Compound X on reduction with LiAlH gives a hydride Y containing 21.72% hydrogen along with other 4 products. The compound Y reacts with air explosively resulting in boron trioxide. Identify X and Y. Give balanced reactions involved in the formation of Y and its reaction with air. Draw the structure of Y. [IIT-2001] 2 9 . Mention two esters produced when a racemic mixture of 2- phehyl propanoic acid is treated with (+) 2- butanol. What is the stereochemical relationship between these esters? [IIT-2003] 3 0 . Carry out following conversion in 3 or less steps. OH Asprine (Acetyl salicylic acid) [IIT-2003] 3 1 . Carry out following conversion in four or less steps. Also mention all the reagents used and reaction conditions. NO2 NO2 [IIT-2004] OH

3 2 . An organic compound P(C H O) reacts 1015 times faster then ethylene with dilute H SO to give two 5 10 24 products Q and R. Both Q and R give positive iodoform test. Identify P, Q and R and also give reason for very high reactivity of P. [IIT-2004] O OH 33. H+/ 1. O3 NaOH (X) (Y) 2. Zn/CH3COOH Identify (X) and (Y). [IIT-2004] 3 4 . Phenyl magnesium bromide reacting with t-Butyl alcohol gives [JEE 2005] (A) Ph – OH (B) Ph – H (C) (D) 3 5 . Statement-1: p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid. [JEE 2007] because Statement-2 : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. (A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1. (B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1. (C) Statement-1 is True, Statement-2 is False. (D) Statement-1 is False, Statement-2 is True. 3 6 . In the reaction OCH3 HBr the products are [JEE 2010] (A) Br OCH3 and H2 (B) Br and CH3Br (C) Br and CH3OH (D) OH and CH3Br

PREVIOUS YEARS QUESTIONS ANSWER KEY EXERCISE -5 1. (B) 2. (D) 3. (D) 4.(A) 5. (C) 6. (D) 7.(B) 8. (D) 9. (A) 10. (C) 11. (B) 12. (A) 13. (C) 14. (C) 15. (D) 16. (A) 1 7 . n-butanol is oxidised by KMnO4 and not t-butanol as the latter does not contain H atom attached to carbinol carbon atom.  CH CH CH CH OH + KMnO  CH CH CH COO O K + MnO + KOH 3222 4 322 2 n-Butanol Brown CH3 CH3 – C – CH3 + KMnO4 No reaction OH t-butanol H Me H H Me -H2O Me 1 8 . CH3 – C – C – CH3 + KMnO4 CH3 – C – C – CH3  OH Me  CH3– CH – C – CH3 H:O.. HMe Me 1,2-methyl shift Me Me CH3– C = C – CH3 –H Me CH3– CH – C – CH3  Me 1 9 . (D) Ph – CH – CH3 C6H5COOH OH (D) (E) 2 0 . The ether formation involves nucleophilic substitution of alkoxide ion for halide ion. R'O + R – X R'O + R – X Slow   Fast R' – O – R + X— R ' O .........R......... X 3° alkyl halide can also involve elimination of HX to give alkene in the presence of a base. So, it is better to start with 3° alkoxide and 1° alkyl halide, i.e., equation (b). OO 21. 23. Due to intermolecular H-bonding O O 2 4 . A = CH3 – C – OH, B=C2H5O18H O Br MgBr BrMgOCHMe HOCHMe Br Me 25. Mg MeCHO H3O HBr Et2O (A) (B) (C) Meachnism

HOCHMe   Br Me H2OCHMe CHMe  Me Me  Br H –H2O 2° carbonium 3° carbonium Br ONa OMe OMe OMe OMe 26. NaOH M e 2SO 4 conc. H2SO4  NaOH  H3O   high Pr essure SO3H ONa OH Alternative rout Br Br Br Br OMe OMe conc. H2SO4  NaOH  Me2SO4  higNhaPOrHessure H3O  SO3H ONa OMe ONa OH 27.   ;  C O2 ; CH2  C OOH ; CH2  CH.C H2OH C H2O R'O + R – X (X) (Y) (Z) 2 8 . X = BCl ; Y = B H 3 26 29. Ph H H CH3– C – COOH + CH3– C – COOH (+) CH3CH2– C – OH H Ph CH3 conc. H2SO4  (racemic mixture) Ph H HH CH3 – C – C – O – C – CH2CH3 + CH3 – C – C – O – C – CH2CH3 HO CH3 Ph O CH3 during esterification reaction only –COOH and –OH participates. There is no effect on structure or configuration of carbon adjacent to these groups. So when (±) acid reacts with pure (+) alcohol two esters are produced which are diastereoisomers of each other. OH OH OCOMe COOH COOH (1) NaOH–CO2 30. , High P MeCOCl (2) H Py

3 1 . NO2 NO2 conc. HNO3 OH conc. H2SO4 H2O 75°C NO2 NO2  NO2 NNCl NH4SH or SnCl2 HCl NO2 NaNO2 - HCl NH2 0° - 5° C CH2 O 32. (P) CH3 – CH2 – O – C – CH3 ; (Q) CH CH OH ; (R) CH3 – C – CH3 32 When ethylene reacts with dil. H SO CH CH  is produced during rate determining step, whereas P gives 24 32 resonance stabilized intermediate. CH3 CH3 CH3 – CH2 – O – C – CH3 CH3 CH2 – O = C – CH3   Due to extra stability of intermediate the rate of reaction is very fast. 33. O (X) OC C CH2 CH2 H 34. B CH3 CH2 CH2 (Y) 35. D 36. D



EXERCISE-01 CHECK YOUR GRASP SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER) 1 . IUPAC name of the hydrocarbon (A) is : CH3 A: (B) 5-ethyl-2methylhexane C2H5 (A) 2-ethyl-5methylhexane (C) 2, 5-dimethylheptane (D) 5-ethyl-2,5-dimethylpentane 2 . IUPAC name of neopentyl group is : (A) 2,2-dimethylbutyl (B) 2, 2-dimethylpropyl (C) 1, 1-dimethylbutyl (D) 1, 1-dimethylpropyl 3 . IUPAC name of the following compouund is : OH CH3 (A) 2-methyl-3-cyclohexenol (B) 3-methyl-1-cyclohexen-4-ol (C) 4-hydroxy-3-methyl-1-cyclohexene (D) 2-hydroxy-1-methylcyclohexene 4 . Which compound is tertiary alcohol ? (A) 1-propanol (B) 2-methyl-1-hexanol (C) 3-methyl-2-hexanol (D) 2-methyl-2-hexanol 5 . 3-Butenoic acid (or But-3-enoic acid) is represented as : OO O (A) (B) (C) (D) none of these OH OH OH OH 6 . In the nomenclature of priority order is – CH3 (A) –CH3 < –OH < C=C (first) (B) –OH<–CH3 < C=C (first) (C) C=C<–CH3 <–OH (first) (D) –CH3 < C=C < – OH (first) 7 . C4H8O2 represents :- (A) An acid only (B) An ester only (C) An ketone only (D) An acid and an ester also 8 . The higher homologue of dimethylamine (CH3—NH—CH3) has the structure :- (A) (CH3)3N (B) CH3—CH2—CH2—NH2 (C) CH3—NH—CH2—CH3 (D) CH3 CH CH3 NH2

9 . The third member of the family of alkenynes has the molecular formula :- (A) C3H2 (B) C5H6 (C) C6H8 (D) C4H4 1 0 . The hetero atoms present in the following compound is/are : NH2 N N (A) 2 (B) 3 (C) 1 (D) 4 1 1 . Which of the following have only 2° H-atom : CH2 (a) (b) (c) CH3 (d) Correct code is : (A) only a and b (B) a, b and d (C) a, c and d (D) All of them 1 2 . Common name of CH2 CH—CN is :- (a) acrylonitrile (b) vinyl cyanide (c) allyl cyanide (d) allyl nitrile (A) a, b and d (B) a and b (C) only b (D) a, b and c 1 3 . Which of the following names is correct :- (A) 4–Isopropyl–3–methyl hexane (B) 2–Ethyl–3–isopropyl pentane (C) 3–Isopropyl–4–methyl hexane (D) 3–Ethyl–2,4–dimethyl hexane 1 4 . The correct systematic IUPAC name of the given compound is : OH CH2 C CH2 C OH COOHCOOH O (A) 3–Carboxy–3–hydroxy butane dioic acid (B) 2–Hydroxy propane–1,2,3–tricarboxylic acid (C) 3–Hydroxy butane dioic acid (D) 2–Bis(carboxymethyl)–2–hydroxy ethanoic acid 1 5 . The IUPAC name of CH3—CH2—NH—CH3 is :- (A) Methyl ethyl amine (B) 1–methyl amino ethane (C) N–methyl ethanamine (D) N–ethyl methanamine 1 6 . The correct IUPAC name from the incorrect name 4–Amino–3–hydroxy–2–butene is :- (A) 1–Amino–2–hydroxy–2–butene (B) 4–Amino–2–buten–3–ol (C) 1–Amino–2–buten–2–ol (D) 1–Amino–2–butenol 1 7 . The correct name of 2–chlorobutan–3–ol is :- (A) 3–Chloro–2–hydroxy butane (B) 3–Chloro–2–butanol (C) 3–Hydroxy–2–chloro butane (D) 2–Chloro–3–hydroxy butane

H 1 8 . The correct name for C O is :- OH (B) 2–Formyl–1–hydroxy cyclopentane (A) 2–Hydroxy cyclopentanal (D) Cyclopentane–2–ol–1–al (C) 2–Hydroxy cyclopentane carbaldehyde 19. The name for the structure H2C CH2 CH2 CH C Cl CH2 CH2 O (A) Cyclo hexanoyl chloride (B) Cyclohexane carbonyl chloride (C) 1–Chloro cyclohexanal (D) Chloro cyclohexyl methanal 2 0 . CH3 O C CH2 COOH O The correct IUPAC name of the above compound is : (A) 2–Acetoxy ethanoic acid (B) 2–Methoxycarbonyl ethanoic acid (C) 3–Methoxyformyl ethanoic acid (D) 2–Methoxyformyl acetic acid CHECK YOUR GRASP ANSWER KEY EXERCISE -1 Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Ans. C B A D A D D C C A B B D B C Que. 16 17 18 19 20 Ans. C B C B B

EXERCISE–02 BRAIN TEASERS SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER) 1 . The IUPAC name of COOH COOHCH3 is :- CH3 CH CH2 CH CH COOH (A) 2,4,5–Hexane tricarboxylic acid (B) 2,3,5–Hexane tricarboxylic acid (C) 2–(1–carboxyethyl)–4–methyl pentanedioic acid (D) 3,5–Dicarboxy–2–methyl hexanoic acid 2 . The name for HC C C CH CH3 is :– CH3 (B) 3–Methyl–3–penten–1–yne (A) 3–Methyl–2–penten–4–yne (C) 3–Methyl–4–pentyn–1–ene (D) 3–Methyl pentenyne Cl 3.  CH3  has the IUPAC name as :- C2H5 (B) 1–Chloro–3–ethyl–2–methylcyclopentane (A) 3–Chloro–1–ethyl–2–methylcyclopentane (C) 4–Chloro–1–ethyl–5–methylcyclopentane (D) None of above 4 . The IUPAC name of CH3CH2NHCHO is : (A) N–formyl ethanamine (B) Ethyl amino methanal (C) N–ethyl methanamide (D) None of them Me Me Me 5 . The IUPAC name of the structure is :- Me Me (A) 2,4,5–Triethyl–3–nonene (B) 5,6–Diethyl–3–methyl–4–decene (C) 2,4,5–Triethyl–3–octene (D) 3–Ethyl–5–methyl–3–heptene 6 . O  has the IUPAC name : COOC2H5 (A) Ethyl–2–oxo cyclopentane carboxylate (B) 2–Cyclopentanone–1–carbethoxy (C) 2–Ethylcarbonate cyclopentanone (D) 1–Keto–2–carbethoxy cyclopentanone HO has the IUPAC name :- 7. (A) 3,4–Dimethyl–1–penten–3–ol (B) Isopropyl–3–methyl vinyl carbinol (C) 2,3–Dimethyl–4–penten–3–ol (D) None of the above

CH3 8 . The IUPAC name of CH2CH3  is :- (A) 1–Methyl–5–ethyl cyclohex–2–ene (B) 5–Ethyl–3–methyl cyclohex–1–ene (C) 4–Ethyl–6–methyl cyclohex–1–ene (D) 1–Ethyl–5–methyl cyclohex–3–ene 9 . In the compound HC C—CH2—CH CH—CH3, the C2—C3 bond is the type of :- (A) sp – sp2 (B) sp3 – sp3 (C) sp – sp3 (D) sp2 – sp2 1 0 . The number of all primary amines possible with the molecular formula C3H9N and the primary amine with amino group on a primary carbon atom is given by the set :- (A) 4 , 1 (B) 2 , 1 (C) 3, 2 (D) 2, 2 1 1 . The number of primary alkanols, secondary alkanols and tertiary alkanols possible with the formula C4H10O is given by the set :- (A) 2, 1, 0 (B) 1, 2, 1 (C) 2, 1, 1 (D) 2, 1, 2 1 2 . IUPAC name of CH = CH – CH NH is : (B) 2-Propen-1-amine 2 22 (A) 3-amino propenamine (C) 3-Amino-1-propenamine (D) Allyl amine 1 3 . Which name is correct : OHC CH3 CH3 (A) CH3 (B) Spiro(3,6) decane 3, 7-Dimethyloct-2,6-dienal I (C) Et N N–Methyl-N-Ethylethanamine 3-Ethyl-7-iodobicyclo (2.2.1) heptane (D) SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS) O 1 4 . The compound CH3—CH2—C—CH2 may be named as : CH3 (A) 2-ethyl-2-methyl oxirane (B) 1, 2-epoxy-2-methylbutane (C) 1,2-oxapentane (D) 2-methyl-2-butoxide 1 5 . Which of the following names are not correct for the given compound : CH2 — CH — CH2 (B) 1,2,3-Triformylpropane CHO CHO CHO (D) Propane-1,2,3-tricarbaldehyde (A) 3-Formyl pentane-1,5-dial (C) 2-Formylbutane-1,4-dial

1 6 . Which of the following names are correct for the compound : O CH3—C—CH2–COOH (A) 3-ketobutan-1-oic acid (B) 4-Carboxy butan -2-one (C) 3-oxo butan-1-oic acid (D) 3-Carboxy acetone 1 7 . The compound C6H5—CH=CH—COOH may be called as : (A) Succinic acid (B) 3-phenylprop-2-en-1-oic acid (C) Mandelic acid (D) Cinnamic acid 1 8 . Which of the following are the names of cyclic ether : (A) Oxirane (B) Epoxyalkane (C) Alkene oxide (D) Carbional 1 9 . The name (s) of the following compound is : (B) Isobutyro nitrile (CH3)2CHCN (D) None of these (A) 2-Methyl propane nitrile (B) 2,3-dihydroxy butane-1,4-dioic acid (C) Isopropyl cyanide (D) None of these 2 0 . The name(s) of the following compound is : CH(OH)COOH CH(OH)COOH (A) tartaric acid (C) '-dihydroxy succinic acid BRAIN TEASERS ANSWER KEY EXERCISE -2 Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 A n s . B B B C B A A B C B C B B A ,B B,C Que. 16 17 18 19 20 A n s . A ,C B,D A ,B,C A ,B,C A ,B,C

EXERCISE–03 MISCELLANEOUS TYPE QUESTIONS MATCH THE COLUMN 1 . Match the following the compounds of column I with column II. Column-I Column-II (A) Wood spirit (p) 2-Butyne (B) Acetone (q) Trichloromethane (C) Dimethyl acetylene (r) Methanol (D) Chloroform (s) Propanone 2 . Match the following the compounds of column I with column II. Column-I Column-II (p) Alkynes (A) CnH2n + 2 (q) Alkenes (B) CnH2n (r) Cyclohexane (C) CnH2n – 2 (s) Paraffins or alkanes (D) C6H12 3 . Match column I with column II and select the correct answer from the given codes : Column-I Column-II (compounds) (number of carbons in the bridges) (A) (p) [3.2.1] (B) (q) [4.3.0] (C) (r) [4.4.0] (D) (s) [3.2.0] COMPREHENSION BASED QUESTIONS : Comprehension # 1 If the organic compond contains more than two similar terminal groups and all of them are directly attached to the principal chain, then none of them forms a part of the principal chain. Special suffixes are used to name these :-

Functional group Suffix –—CONH2 Carboxamide –—CN Carbonitrile –—CHO Carbaldehyde —COOH Carboxylic acid Carbon atoms of these terminal groups are not counted in the principal chain. If any one of these terminal groups is not directly attached to the parent chain and forms the part of side chain, then the longest chain is selected containing two such similar groups at its two ends. The groups present in the side chain are treated as substituents and are indicated by suitable prefixes. Indicate whether the following IUPAC names are true (a) or false (b) COOH 1 . HOOC—CH2—CH—CH2—COOH Propane-1,2,3-tricarboxylic acid True (a) False (b) CN 2 . NC—CH2—CH—CH2—CN 3-cyanopentane-1,5-dinitrile True (a) False (b) CH2COOH 3-(carboxymethyl)-1,5-dioic acid 3 . HOOC—CH2—CH—CH2—COOH False (b) True (a) CH2CHO 3-(formylmethyl)pentane-1,5-dial 4 . OHC—CH2—CH—CH2—CHO False (b) True (a) CONH2 Propane-1,2,3-tricarboxamide 5 . H2NOC —CH2—CH—CH2—CONH2 False (b) True (a) Comprehension # 2 In addition to the standard ring systems (such as cyclohexane), cyclic compounds can also be bicyclic, tricyclic, etc. or they can be spirocyclic, bicyclic or bridge head carbons. The point of attachment of two rings are called bridge head atoms. The formal names of bicyclic and related ring systems are based on (a) Total numbe of atoms in the molecule. (b) The number of atoms in each bridge connecting the bridge head atoms. These numbers are written in square bracket in decreasing order. Spirocyclic compounds have two fused rings, but only one bridge head atom. Spirocyclic compounds are named like bicyclic compounds, but have the prefix spirocyclo. Answer the following question : 1. what is the IUPAC name of the above compound ? (A) cyclo [1.2.2] heptane (B) Bicyclo [1.2.2] heptane (C) Bicyclo [2.2.1] heptane (D) cyclo [2.2.1] heptane

2 . The number of atoms in each bridge are : (A) [3.2.1] (B) [3.1.0] (C) [1.3.0] (D) [2.1.0] 3 . Select the correct statements about the following compounds : (A) It is a tricyclic compound (B) It is bicyclo compound (C) It is spiro compound (D) Its IUPAC name is bicyclo [2.2.2] hexane 4 . Which of the following is the correct structure of bicyclo [1.1.0] butane ? CH2—CH2 CH2—CH (A) (B) (C) (D) CH2 CH2—CH2 CH2—CH Comprehension # 3 Branched- chain alkanes are named according to the following rules. (1) Longest chain Rule - Locate the longest continuous chain of carbon atoms. This chain determines the parent name of the alkane. (2) Lowest set of locants - The longest continuous chain are numbered by arabic numerals 1, 2, 3, 4, .... from one end of chain to the other, in such a manner that carbon atom carrying first substituent gets the lowest number. (3) Name of the branched chain alkane - The substituent name and the parent alkane are joined in one word and there is a hyphen between the number and the substituent name. (4) Alphabetical order of the side chains - When two or more substituents are present, give each substituent a number corresponding to its position on the longest chain, the substituent group should be listed alphabetically. (5) Numbering of different alkyl groups at equivalent positions- If two different alkyl groups are present at equivalent positions the numbering of the parent chain is done in such a way that alkyl group which comes first in the alphabetical order gets the lower number. (6) Naming of same alkyl groups at different positions - When two or more substituents are identical, indicate this by the use of prefixes di, tri, tetra and soon. Commas are used to separate numbers from each other. (7) Rule for larger number of substituents - If a compound has two or more chains of the same length, the parent hydrocarbon is the chain with the greater number of substituents. (8) Numbering the complex substituent - Name such as iso-propyl, sec-butyl and tert-butyl are acceptable substituent name in the IUPAC system of nomenclature but systematic name are preferable. Systematic substituent names are obtained by numbering the substituent starting at the carbon that is attached to the parent hydrocarbon. This means that the carbon that is attached to the parent hydrocarbon is always the number –1carbon of the substituent. CH3 CH3 1 . In following compound CH3—CH2—C—CH—CH—CH2—CH3 CH3CH3 The correct lowest set of locant is :- (A) 3, 3, 4, 5 (B) 3, 4, 5, 5 (C) 4, 5, 3, 3 (D) 5, 5, 4, 3

2 . The IUPAC name of the compound is ? CH3—CH—CH2—CH2—CH3 CH3—CH2—CH—CH—CH—CH2—CH3 CH3 CH2—CH3 (A) 5-Ethyl-3-Methyl-4-(1-Methylpropyl) octane (B) 4-Ethyl-6-Methyl-5-(1-Methylpropyl) octane (C) 3-Ethyl-5-Methyl-4-(1-Methylpropyl) octane (D) 4-Sec-butyl-5-Ethyl-5-Methylheptane 3 . The correct IUPAC name of the following compound is - CH3—CH2—CH2—CH—CH2—CH2—CH—CH3 CH—CH3 CH3 CH3 (B) 2, 6-Dimethyl-5-propylheptane (A) 2-Methyl-5-isopropyloctane (D) 4-(1-Methylethyl)-7-methyloctane (C) 5-isopropyl-2-Methyloctane 4 . The molecular weight of following compound is 3, 7 - Diethyl -2, 2-dimethyl-4-propylnonane :- (A) 230 (B) 236 (C) 254 (D) 240 5 . The correct IUPAC name of following compound is - CH3 CH3—C—CH2—CH2—CH—CH2—CH2—CH2—CH3 CH3 CH3—C—CH3 CH3—CH—CH3 (A) 2, 3, 3, 7, 7 Pentamethyl-4-butyloctane (B) 4-Butyl-2, 3, 3, 7, 7 pentamethylnonane (C) 2, 2-Dimethyl-5-(1', 1', 2'-trimethylpropyl)nonane (D) 5-(1', 1', 2'-trimethylpropyl)-2, 2-dimethylnonane MISCELLANEOUS TYPE QUESTION ANSWER KEY EXERCISE -3  Match the Column 3. F 4. T 5. T 1. A - (r), B - (s), C - (p), D - (q) 3. (B) 4. (A) 5. (C) 2. A - (s), B - (q, r), C - (p), D - (q, r) 3. (A) 4. (C) 3. A - (q), B - (r), C - (s), D - (p)  Comprehension Based Questions Comprehension #1 : 1. T 2. F Comprehension #2 : 1. (C) 2. (B) Comprehension #3 : 1. (A) 2. (C)

EXERCISE–04 CONCEPTUAL SUBJECTIVE EXERCISE 1 . A cartain substances contains only carbon and hydrogen and has a molecular weight of 70. Photochemical chlorination gave only one monochloride. Write the structure and IUPAC name of the hydrocarbon and its monochloride. 2 . A hydrocarbon of molecular weight 72 g mol–1 has a 2-methyl group. What is the IUPAC name ? Also drawn its bond-line structure ? 3 . Write the structure and give IUPAC systematic name of an alkane or cycloalkane with the formula : (a) C H that has only primary hydrogen atoms 8 18 (b) C H that has only secondary hydrogen atoms. 6 12 4 . What is wrong with the names given for these compounds provide the correct name for each : (i) (ii) 2-ethyl-2-pentene 3-cyclohexylpropane (iii) (iv) 1, 3, 4-trimethylcyclo-pentane 2, 2-methylbutylcyclopentanol 5 . Write the IUPAC name for each the following structures : (a) (b) (c) 6 . Write down the correct priority for citation as principal groups : O —C— , —COOH, —CHO, —OH, —Br, —. 7 . Write down the correct IUPAC name of the following compounds : CH3 CH3 CN (i) CH3—C=C—CH—C—CH—C—OC2H5 (ii) —C—O—CH—CH3 OO O CH3 OH O 1' 2' 3' 4' 1 CH2CH2COCH3 (iii) 2

8 . Write down the structure of the given compounds : (i) Bicyclo [4.3.1] decane (ii) 1-(3'-methylcyclopentyl) benzene (iii) 4-ethyl-2-methyl-1-propylcyclohexane 9 . Answer the following : (i) What would be the molecular formula for a straight chain hydrocarbon having 8 carbon atoms with (a) all C—C single bond, (b) Three C—C double bond, (c) one C—C triple bond and one C—C double bond. (ii) What is the minimum number of carbon atoms in (a) a branched alkane, (b) cyclo-alkane 1 0 . Give the IUPAC names of the following compounds : CH3 (ii) CH (COOH) (iii) CH3—CH=C—CH2—COOH (i) H3C —N—C—CH2—CH3 22 CH3C2H5 CONH2 CONCEPTUAL SUBJECTIVE EXERCISE ANSWER KEY EXERCISE -4 1. and —Cl CH3 2. CH3—CH—CH2—CH3 CH3 CH3 6. –COOH > –CHO >–C– >–OH>–Br 3. (a) CH3—C — C—CH3 (b) O CH3 CH3 7. (a) Ethyl-2-cyano-5-cyclopropyl-4, 6-dimethyl-3-oxohept-5-en-1-oate (b) Isopropyl-3-hydroxycyclohexane carboxylate. (c) 2-(3'-oxobutyl) cyclohexan-1-one. CH3CH2CH2 CH2CH3 8. (i) (ii) CH3 (iii) CH3 9. (i) (a) C H (b) C H (c) C H (ii) (a) 4 (b) 3 8 18 8 12 8 12 10. (i) 3-(N, N-dimethylamino) -3-methyl pentane; (ii) propan-1, 3-dioic acid (iii) 3-Carbamoylpent-3-enoic acid

EXERCISE–05(A) PREVIOUS YEARS QUESTIONS 1 . Underlined carbon is sp hybridised in- [AIEEE -2002] [AIEEE -2002] (1) CH3CH=CH2 (2) CH3CH2–NH2 (3) CH3CONH2 (4) CH3CH2CN 2 . Which of the following compound has wrong IUPAC name? (1) CH CH —CH COO—CH CH (Ethyl butanoate) 32 2 23 (2) CH3  CH  CH2  CHO (3-Methylbutanal) | CH3 (3) CH3 CH CH CH3 (2-Methyl-3-butanol) OH CH3 (4) CH3 CH C CH2 CH3 (2-Methyl-3-pentanone) CH3 O [AIEEE-2003] [AIEEE-2003] 3 . The IUPAC name of CH3COCHCH3 2 is [AIEEE -2004] [AIEEE-2004] (1) isopropyl methyl ketone (2) 2-methyl-3-butanone [AIEEE-2006] (3) 4-methylisopropyl ketone (4) 3-methyl-2-butanone 4 . The general formula of CnH2nO2 could be for open chain (1) diketones (2) carboxylic acids (3) diols (4) dialdehydes 5 . Which one of the following does not have sp2 hybridised carbon ? (1) Acetone (2) Acetic acid (3) Acetonitrile (4) Acetamide 6 . The IUPAC name of the compound is HO (1) 1, 1-dimethyl-3-cyclohexanol (2) 1, 1-dimethyl-3-hydroxy cyclohexane (3) 3, 3-dimethyl-1-cyclohexanol (4) 3, 3-dimethyl-1-hydroxy cyclohexane 7 . The IUPAC name of the compound is Cl Br (1) 6-bromo-2-chlorocyclohexene (2) 3-bromo-1-chlorocyclohexene (3) 1-bromo-3-chlorocyclohexene (4) 2-bromo-6-chlorocyclohex-1-en

8 . The IUPAC name of is- [AIEEE-2007] (1) 1, 1-diethyl-2, 2-dimethylpentane (2) 4, 4-dimethyl-5, 5-diethylpentane (3) 5, 5-diethyl-4, 4-dimethylpentane (4) 3-ethyl-4, 4-dimethylheptane 9 . The correct decreasing order of priority for the functional groups of organic compounds in the IUPAC system of nomenclature is [AIEEE -2008] (1) –COOH, – SO H, –CONH , –CHO 32 (2) –SO H, –COOH, –CONH , – CHO 32 (3) –CHO, – COOH, –SO H, –CONH 32 (4) –CONH , –CHO, –SO H, –COOH 23 1 0 . The IUPAC name of neopentane is :- (1) 2–methylpropane [AIEEE -2009] (2) 2, 2–dimethylbutane (3) 2–methylbutane (4) 2, 2–dimethylpropane O 1 1 . The IUPAC name of the compound H2C CH – CH3 is :- [AIEEE-2012 (Online)] [AIEEE-2012 (Online)] (1) 1, 2-Epoxy propane (2) Propylene oxide (3) 1, 2–Oxo propane (4) 1, 2–Propoxide 1 2 . The IUPAC name of the following compounds is : CH3 H C=C H CC–CH2CH3 (1) (Z) – 5 – hepten – 3 – yne (2) (Z) – 2 – hepten – 4 – yne (3) (E) – 5 – hepten – 3 – yne (4) (E) – 2 – hepten – 4 – yne PREVIOUS YEAR QUESTIONS ANSWER KEY EXERCISE-05(A) Que. 1 2 3 4 5 6 78 9 10 11 12 3 24 14 1 4 Ans 4 3 4 2 3

EXERCISE–05(B) PREVIOUS YEARS QUESTIONS 1 . The IUPAC name of the compound, CH2=CH—CH(CH3)2 is - [IIT-88] [IIT-90] (A) 1,1-Dimethylprop-2-ene (B) 3-Methylbut-1-ene (C) 2-Vinylpropane (D) 1-Isopropylethylene 2 . The correct IUPAC name of the compound is : CH3 (B) 5,6–diethyl–3–methyl dec–4–ene CH3–CH2C=CH–CHCH2CH3 (D) 2,4,5–triethyl–3–ene CH3CH2–CH–CH2CH2CH2CH3 (A) 5,6–diethyl–8–methyl dec–6–ene [IIT-91] (C) 6–butyl–5–ethyl–3–methyl oct–4–ene 3 . The IUPAC name of - OHCCH=CH–CH–CH=CH2 (B) 4–Butylhexa–2,5–dien–1–al is - (D) 3–Butylhexa–1,4–dien–8–al CH2CH2CH2CH3 (A) 5–Vinyloct–3–en–1–al (C) 5–Vinyloct–5–en–8–al 4 . Choose the cor rect IUPAC name for CH3–CH–CHO is - [IIT-93] CH2–CH3 (A) Butan–2–aldehyde (B) 2–Methylbutanal (C) 3–Methyl iso butyraldehyde (D) 2–Ethylpropanal 5 . A compound with molecular formula C8H14, contains 12 secondary and two tertiary H atoms. The compound is : [IIT-93] (A) (B) (C) (D) O [IIT-06] 6 . IUPAC name of C6H5 – C – Cl (B) Benzenecarbonylchloride (A) Benzoylchloride (D) Phenylchloroketone (C) Chlorophenyl ketone PREVIOUS YEARS QUESTIONS ANSWER KEY EXERCISE -5 (B)  1. B 2. B 3. B 4. B 5. B,C,D 6. B



EXERCISE-01 CHECK YOUR GRASP SELECT THE CORRECT ALTERNATIVE (ONLY ONE CORRECT ANSWER) 1 . A white crystalline solid A on boiling with caustic soda solution gave a gas B which when passed through an alkaline solution of potassium mercuric iodide gave a brown ppt. The substance A on heating gave a gas C which rekindled a glowing splinter but did not give brown fumes with nitric oxide. The gas B is ? (A) H2S (B) NH3 (C) HCl (D) CO2 2 . The gas C (in the above question) is - (A) N2O (B) O2 (C) NO (D) O3 3 . A metal oxide is yellow when hot and white when cold. The metal oxide is - (A) ZnO (B) CuO (C) PbO (D) All 4 . When a salt is heated with dil. H2SO4 and KMnO4 solution, the pink colour of KMnO4 is discharged, the mixture may contain ? (A) Sulphite (B) Carbonate (C) Nitrate (D) Bicarbonate 5 . Sulphur dioxide may be recognised by its ? (A) Characteristic pungent smell of burning sulphur (B) Ability to turn dichromate paper green (C) Ability to decolourize acidified KMnO4 solution (D) All 6 . Chromyl chloride vapours are dissolved in water and solution is treated with acetic acid and lead acetate solution is added, then- (A) The solution will remain colourless (B) The solution will become dark green (C) A yellow solution will be obtained (D) A yellow precipitate will be obtained 7. In a combination of N O – , Br– and I– present in a mixture, Br– and I– interfere in the ring test for N O – . 3 3 These are removed by adding a solution of - (A) AgNO3 (B) Ag2SO4 (C) Ag2CO3 (D) None of these 8 . A dark green bead in borax bead test indicates the presence of - (A) Cr3+ (B) Mn2+ (C) Co2+ (D) Ni2+ 9 . Lead has been placed in group 1st and 2nd because - (A) It shows the valency one and two (B) It forms insoluble PbCl2 (C) It forms lead sulphide (D) Its chloride is partly soluble in water 1 0 . The group reagent for third group is NH4OH in presence of - (A) (NH4)2CO3 (B) NaCl (C) (NH4)2SO4 (D) NH4Cl 1 1 . What would you observe if you add with shaking excess of dilute NaOH solution to an aqueous solution of AlCl3 ? (A) A permanent white ppt. is formed (B) No change at first, but a white ppt. is formed on standing (C) A white ppt. is formed which later dissolves (D) A green ppt. which turns red on standing in air 1 2 . BaCl2 solution gives a white ppt. with a solution of an acid radical which dissolves in dil. HCl with the evolution of a colourless, pungent smelling gas. The acid radical may be ? (A) SO 2– (B) S2– (C) SO 2– (D) C O 2 – 4 3 3

1 3 . K3Co(NO2)6 is known as - (A) Fischer's salt (B) Thenard's blue (C) Rinman's green (D) Blue vitriol 1 4 . In the precipitation of the iron group in qualitative analysis, ammonium chloride is added before adding ammonium hydroxide to - (A) Decrease concentration of OH– ions (B) Prevent interference by phosphate ions (C) Increase concentration of Cl– ions (D) Increase concentration of N H  ions 4 1 5 . Potassium ferrocyanide is used in the detection of - (A) Cu2+ ion (B) Fe3+ ions (C) Both (D) None 1 6 . The acidic solution of a salt produced a deep blue colour with starch iodide solution. The salt may be- (A) Chloride (B) Nitrite (C) Acetate (D) Bromide 1 7 . Which of the following pairs of ions would be expected to form precipitate when dilute solutions are mixed? (A) Na+, SO 2  (B) NH  , CO 2  (C) Na+, S 2 (D) Fe3+, P O 3  4 4 3 2 4 1 8 . Nessler’s reagent is ? (A) K2HgI4 (B) K2HgI4 + KOH (C) K2HgI2 + KOH (D) K2HgI4 + KI 1 9 . When bismuth chloride is poured into a large volume of water the white precipitate produced is ? (A) Bi(OH)3 (B) Bi2O3 (C) BiOCl (D) Bi2OCl3 2 0 . Fe(OH)3 can be separated from Al(OH)3 by addition of ? (A) Dil. HCl (B) NaCl solution (C) NaOH solution (D) NH4Cl and NH4OH 2 1 . Mark the compound which turns black with NH4OH? (A) Lead chloride (B) Mercurous chloride (C) Mercuric chloride (D) Silver chloride 2 2 . If NaOH is added to an aqueous solution of zinc ions a white precipitate appears and on adding excess NaOH, the precipitate ? (A) Cationic part (B) Anionic part (C) Both in catonic and anionic parts (D) There is no zinc ion in the solution. 2 3 . A substance on treatement with dil. H2SO4 liberates a colourless gas which produces (i) turbidity with baryta water and (ii) turns acidified dichromate solution green. The reaction indicates the presence of ? (A) CO 2  (B) S2– (C) SO 2  (D) NO  3 3 2 2 4 . An aqueous solution of colourless metal sulphate M, gives a white ppt. with NH4OH. This was soluble in excess of NH4OH. On passing H2S through this solution a white ppt. is formed. The metal M in the salt is ? (A) Ca (B) Ba (C) Al (D) Zn 2 5 . The salt used for performing ‘bead’ test in qualitative inorganic analysis is ? (A) K2SO4. Al2 (SO4)3. 24 H2O (B) FeSO4. (NH4)2SO4.6H2O (C) Na (NH4) HPO4. 4H2O (D) CaSO4. 2H2O 2 6 . A chloride dissolves appreciably in cold water. When placed on a platinum wire in Bunsen flame no distinc- tive colour is noticed, the cation would be ? (A) Mg2+ (B) Ba2+ (C) Pb2+ (D) Ca2+ 2 7 . Which is not dissolved by dil. HCl ? (A) ZnS (B) MnS (C) BaSO3 (D) BaSO4

28. The brown ring test for NO  and NO  is due to the formation of complex ion with formula – 2 3 (A) [Fe (H2O)6]2+ (B) [Fe (NO) (CN)5]2– (C) [Fe (H2O)5NO]2+ (D) [Fe (H2O) (NO)5]2+ 2 9 . Which of the following metal sulphides has maximum solubility in water - (A) HgS Ksp = 10–54 (B) CdS Ksp = 10–30 (C) FeS Ksp = 10–20 (D) ZnS Ksp = 10–22 3 0 . Which one of the following statement is correct - (A) From a mixed precipitate of AgCl and AgI, ammonia solution dissolves only AgCl (B) Ferric ions give a deep green precipitate on adding potassium ferrocyanide solution (C) On boiling a solution having K+, Ca2+ and H CO – ions we get a precipitate of K2Ca(CO3)2 3 (D) Manganese salts give a violet borax bead test in the reducing flame 31. When H2S is passed through H g 2  , we get - 2 (A) HgS (B) HgS + Hg2S (C) HgS + Hg (D) Hg2S 3 2 . Potassium chromate solution is added to an aqueous solution of a metal chloride. The precipitate thus obtained are insoluble in acetic acid. These are subjected to flame test, the colour of the flame is - (A) Lilac (B) Apple green (C) Crinison red (D) Golden yellow 3 3 . Sometimes yellow turbidity appears while passing H2S gas even in the absence of II group radicals. This is because of - (A) Sulphur is present in the mixture as impurity (B) IV group radicals are precipitated as sulphides (C) The oxidation of H2S gas by some acid radicals (D) III group radicals are precipitated as hydroxides 3 4 . A metal salt solution gives a yellow ppt with silver nitrate. The ppt dissolves in dil. nitric acid as well as in ammonium hydroxide. The solution contains - (A) Bromide (B) Iodide (C) Phosphate (D) Chromate 3 5 . A blue colouration is not obtained when - (A) Ammonium hydroxide dissolves in copper sulphate (B) Copper sulphate solution reacts with K4[Fe(CN)6] (C) Ferric chloride reacts with sodium ferrocyanide (D) Anhydrous white CuSO4 is dissolved in water 3 6 . A pale green crystalline metal salt of M dissolves freely in water. On standing it gives a brown ppt on addition of aqueous NaOH. The metal salt solution also gives a black ppt on bubbling H2S in basic medium. An aqueous solution of the metal salt decolourizes the pink colour of the permanganate solution. The metal in the metal salt solution is - (A) Copper (B) Aluminium (C) Lead (D) Iron CHECK YOUR GRASP ANSWER KEY EXERCISE -1 Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Ans. B A A A D D B A D D C C A A C B D B C C Que. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 Ans. B B C D C A D C C A C B C C B D

EXERCISE-02 BRAIN TEASERS SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS) 1 . Identify the incorrect reaction (s) - (A) K2Cr2O7 + 4NaCl + 3H2SO4 (conc.)  2CrO2Cl2 + 2Na2SO4 + K2SO4 + 3H2O (B) K2Cr2O7 + 6KI + 7H2SO4 (conc.)  3I2 + Cr2(SO4) + 4K2SO4 + 7H2O (C) K2Cr2O7 + 4AgCl + 3H2SO4 (conc.)  2CrO2Cl2 + 2Ag2SO4 + K2SO4 + + 3H2O (D) MnO2 + NaCl + 2H2SO4 (conc.)  NaHSO4 + MnSO4 + HCl + H2O + 1/202 2 . Which of the following statment (s) is (are) ture - (A) Cu2+ salts form soluble complex with excess KCN (B) Cu2+ salts form soluble complex with aqueous ammonia (C) Cu2+ salts form soluble complex with KI (D) A piece of iron or zinc when place in Cu2+ salt solution, Precipitates copper 3 . A mixture of two white substances was dissolved in water. On passing Cl2 gas through the solution a deep brown colour is developed. Addition of BaCl2 solution to the original solution gives a white ppt. Addition of a large amount of NaOH solution to the original solution gives a white ppt, whose suspension in water is used as an ant-acid, the mixture gives golden yellow colour flame. What is the chemical composition of the mixture - (A) NaBr & MgSO4 (B) NaBr & CaSO4 (C) NaBr & Al2(SO4)3 (D) NaBr & ZnSO4 4 . KBr + MnO2 + H2SO4 (conc.)  KHSO4 + MnSO4 + H2O + [X] (unbalanced equation) - (A) X turns starch paper orange red (B) X with AgNO3 solution gives a pale yellow ppt which is completely soluble in excess ammonium hydroxide (C) X produces violet colour in organic layer in Kl solution (D) X is liberated when a mixture of KBr, K2Cr2O7 and conc. H2SO4 is heated 5 . An inorganic lewis acid [X] gives gelatinous white ppt. With NH4OH in presence of NH4Cl. [X] will respond to which of the following characteristics - (A) X fumes in moist air (B) X on heating with solid K2Cr2O7 and conc. H2SO4 gives deep red or orange red fumes (C) X on addition of excess NaOH gives white ppt (D) X on heating with Na2CO3 and cobalt nitrate gives a blue bead in oxidising flame 6 . SO2 and CO2 both turn lime water (A) milky, SO2 also turns K2Cr2O7/H+ (B) green while O2 is soluble in pyrogallol (C) turning it black. These gases are to detected in order by using these reagents. The order is - (A) (A), (B), (C) (B) (B), (C), (A) (C) (B), (A), (C) (D) (A), (C), (B) 7. Three test tubes A, B, C contain P b2+, H g 2  and Ag+ (but unknown). To each aqueous solution NaOH 2 is added in excess. Following changes occur - A : Black ppt B : Brown ppt C : White ppt but dissolves in excess of NaOH A, B and C contain respectively : (A) Pb 2+, H g 2 and Ag+ (B) H g 2  , Ag+, Pb2+ 2 2 (C) Ag+, Pb2+, Hg22 (D) Ag+, H g 2  and Pb2+ 2

8 . Of the following oxides, all are soluble in NaOH(aq) except - (A) ZnO (B) Al2O3 (C) Fe2O3 (D) SnO2 9 . The solvay process can be represented by the following scheme CaCO3 CaO + CO2 H2O NH3+H2O A B NaHCO3 + D NaCl C+H2O NH3+H2O+E In the above process, the correct options are : (A) A = Ca(OH)2 (B) B = NH4HCO3 (C) E = CaCl2 (D) C = NaHCO3 1 0 . Reddish brown gas is obtained when the following are treated with conc. H2SO4 : (A) Br– (B) N O – (C) NO – (D) I– 3 2 1 1 . KI solution identifies - (A) Hg 2  (B) Pb2+ (C) Ag+ (D) Cu2+ 2 1 2 . The only cations present in a slightly acidic solution are Fe3+, Zn2+ and Cu2+. The reagent that when added in excess to this solution would identifiy and separate Fe3+ in one step is - (A) 2 M HCl (B) 6 M NH3 (C) 6 M NaOH (D) H2S gas 1 3 . A test-tube containing a nitrate and another containing a bromide and MnO2 are treated with conc. H2SO4. The brown fumes evolved are passed in water. The water will be coloured by - (A) The nitrate (B) The bromide (C) Both (D) None of the two 1 4 . Production of a green edged flame on igniting the vapours evolved by heating a given inorganic salt with a few ml of ethanol and conc. H2SO4 indicates the presence of - (A) Tartrate (B) Oxalate (C) Acetate (D) Borate 1 5 . When CS2 layer containing both Br2 and I2 is shaken with excess of Cl2 water, the violet colour due to I2 disappears and orange colour due to Br2 appears. The disappearance of violet colour is due to the formation of - (A) I3– (B) HIO3 (C) ICI2 (D) I– 1 6 . Which one among the following pairs of ions cannot be separated by H2S in dilute hydrochloric acid- (A) Bi3+, Sn4+ (B) AI3+, Hg2+ (C) Zn2+, Cu2+ (D) Ni2+, Cu2+ 1 7 . Yellow ammonium sulphide solution is a suitable reagent for the separation of - (A) HgS and PbS (B) PbS and Bi2S3 (C) Bi2S3 and CuS (D) CdS and As2S3 1 8 . What product is formed by mixing the solution of K4[Fe(CN)6] with the solution of FeCl3 - (A) Ferro-ferricyanide (B) Ferric-ferrocyanide (C) Ferri-ferricyanide (D) None

1 9 . Which of the following will not give positive chromyl chloride test- (A) Copper chloride, CuCl2 (B) Mercuric chloride, HgCl2 (C) Mercurous chloride, HgCl2 (D) Zinc chloride, ZnCl2 2 0 . When chlorine water is added to an aqueous solution of potassium halide in presence of chloroform, a violet colour is obtained. On adding more of chlorine water, the violet colour disappears, and a colourless solution is obtained. This test confirms the presence of the following in aqueous soultion - (A) Iodide (B) Bromide (C) Chloride (D) Iodide and bromide 2 1 . Which compound does not dissolve in hot dilute HNO3 - (A) HgS (B) PbS (C) CuS (D) CdS 2 2 . An aqueous solution of FeSO4, Al2(SO4)3 and chrome alum is heated with excess of Na2O2 and filtered. The materials obtained are - (A) A colourless filterate and a green residue (B) A yellow filtrate and a green residue (C) A yellow filtrate and a brown residue (D) A green filtrate and a brown residue 2 3 . Three separate samples of a solution of a single salt gave these results. One formed a white precipitate with excess ammonia solution, one formed a white precipitate with dil. NaCl solution and one formed a black precipitate with H2S. The salt could be - (A) AgNO3 (B) Pb(NO3)2 (C) Hg(NO3)2 (D) MnSO4 2 4 . A white sodium salt dissolves readily in water to give a solution which is neutral to litmus. When silver nitrate solution is added to the solution, a white precipitate is obtained which does not dissolve in dil. HNO3. The anion could be - (A) CO 2 – (B) Cl– (C) SO 2– (D) S2– 3 4 2 5 . In the separation of Cu2+ and Cd2+ in 2nd group qualitative analysis of cations, tetrammine copper (II) sulphate and tetrammine cadmium (II) sulphate react with KCN to form the corresponding cyano complexes. Which one of the following pairs of the complexes and their relative stability enalbles the separation of Cu2+ and Cd2+ : (A) K3[Cu (CN)4] more stable and K2 [Cd (CN)4] less stable (B) K2[Cu (CN)4] less stable and K2 [Cd (CN)4] more stable (C) K2[Cu (CN)4] more stable and K2 [Cd (CN)4] less stable (D) K3[Cu (CN)4] less stable and K2 [Cd (CN)4] more stable 2 6 . When K2Cr2O7 crystals are heated with conc. HCl, the gas evolved is - (A) O2 (B) Cl2 (C) CrO2Cl2 (D) HCl 2 7 . On the addition of a solution containing CrO 2– ions to the solution of Ba2+, Sr2+ and Ca2+ ions, the ppt 4 obtained first will be of - (A) CaCrO4 (B) SrCrO4 (C) BaCrO4 (D) A mixture of all the three 2 8 . A mixture of chlorides of copper, cadmium, chromium, iron and aluminium was dissolved in water acidified with HCl and hydrogen sulphide gas was passed for sufficient time. It was filtered, boiled and a few drops of nitric acid were added while boiling. To this solution ammonium chloride and sodium hydroxide were added in excess and filtered. The filtrate shall give test for - (A) Sodium and iron (B) Sodium, chromium and aluminium (C) Aluminium and iron (D) Sodium, iron, cadmium and aluminium

2 9 . A salt on treatment with dil. HCl gives a pungent smelling gas and a yellow precipitate. The salt gives green flame when tested. The solution gives a yellow precipitate with potassium chromate. The salt is- (A) NiSO4 (B) BaS2O3 (C) PbS2O3 (D) CuSO4 3 0 . CrO3 dissolves in aqueous NaOH to give - (A) Cr2O 2 – (B) CrO 2– (C) Cr(OH)3 (D) Cr(OH)2 7 4 3 1 . A mixture of two salts is not water soluble but dissolves completely in dil HCl to form a colourless solution. The mixture could be - (A) AgNO3 and KBr (B) BaCO3 and ZnS (C) FeCl3 and CaCO3 (D) Mn(NO3)2 and MgSO4 3 2 . Which of the following combinations in an aqueous medium will give a red colour or precipitate - (A) Fe3+ + SCN– (B) Fe2+ + [Fe(CN)6]3– (C) Ni2+ + dimethylglyoxime + NH3 solution (D) Cu2+ + [Fe (CN)6]–4 3 3 . Acidic K2Cr2O7 reacts with H2S to produce- (A) Cr6+ ions (B) Cr3+ ions (C) SO2 (D) S 3 4 . A yellow precipitate is obtained when - (A) Lead acetate solution is treated with K2CrO4 (B) Pb(NO3)2 solution is treated with K2CrO4 (C) AgNO3 solution treated with KI (D) H2S is passed through a solution of CdSO4 3 5 . Which of the following ions can be separated by using NH4Cl and NH4OH - (A) Fe3+ and Cr3+ (B) Cr3+ and Co2+ (C) Cr3+ and Al3+ (D) Al3+ and Ba2+ 3 6 . Al2(SO4)3 + NH4OH  X Select the correct statement (s) about compound X : (A) X is a white coloured compound (B) X is insoluble in excess of NH4OH (C) X is soluble in NaOH (D) X can be used as an antacid 3 7 . Which of the following cations cannot be separated by adding NH4Cl, NH4OH and (NH4)2CO3 to their solution ? (A) Ca2+ and Sr2+ (B) Ba2+ and Sr2+ (C) Ba2+ and Mg2+ (D) Ca2+ and Ba2+ 3 8 . On being heated, which of the following substances will give a gas that turns limewater milky ? (A) Na2CO3 (B) ZnCO3 (C) ZnSO3 (D) MgCO3 3 9 . On being heated, which of the following substances will give a white sublimate ? (A) NH4Cl (B) HgCl2 (C) AgCl (D) Hg2Cl2 4 0 . On being strongly heated, which of the following substances will leave a black residue ? (A) CuSO4.5H2O (B) ZnCO3 (C) PbCO3 (D) MnSO4 4 1 . Which of the following cations will turn a borax bead green in an oxidising flame ? (A) Fe2+ (B) Mn2+ (C) Cr3+ (D) Cu2+ 4 2 . Which of the following cations will turn a borax bead blue in an oxidising flame ? (A) Fe3+ (B) Fe2+ (C) Co2+ (D) Cu2+ 4 3 . Which of the following substances are blue ? (A) Fe(BO2)2 (B) CoAl2O4 (C) Co(BO2)2 (D) NaCoPO4