MS CHAUHAN ADVANCE

500 CO2H 24. HO (1) CH2N 2 (A) (de-colourises Br2 water) OH ¾¾¾¾¾¾¾® (2) acetone H+ OH (3)Ac2O, Acetic anhydride Product (A) of the above reaction is : CO2CH3 CO2CH3 OAc (a) O O OAc OC (b) O CO2Ac CH3 CH3 CO2H (c) O OMe (d) AcO O OMe OMe 25. A rather interesting example of the Wolff rearrangement with 2-diazocyclohexanone in methanol is given below. Identify the major product : O N2 CH3OH/light O OCH3 (b) (a) CO2CH3 O O O (d) C ¾ O ¾ H (c) 26. The orbital picture of a singlet carbene (:CH 2 ) can be drawn as : Hp Hp (a) C (b) C H H sp2 sp2 https://t.me/studyzee

501 py pz (c) C H (d) none of these H 27. The orbital picture of a triplet carbene can be drawn as : H p Hp (a) C (b) C H sp2 H sp2 H py pz (c) (d) none of these C H 28. ¾C¾HC¾¾l3 ®( A) ¾C¾HC¾¾l3 ®(B) ; Product (B) is : (a) KOH KOH Cl Cl Cl (b) Cl Cl Cl Cl (c) (d) Cl ? 29. Select the suitable reagent for above conversion. (a) CH 2N 2 / D (b) CBr4 / RLi (c) H 2C == CH 2 (d) t-BuOK https://t.me/studyzee

502 30. HO HO CH2I2 (2 mole) A Product (A) will be : Zn (Cu) (97%) HO (b) HO HO (a) HO (c) HO HO (d) CH3O OCH3 31. The major product formed in the following reaction is Me Me + :CH 2 (singlet) ¾¾® HH H Me Me Me Me CH2CH3 (a) (b) H HH H Me (c) 50 : 50 mixture of above two compounds(d) H H Br 32. O Br H O To carry out above conversion reagent used in decreasing order. (a) Na liq.NH 3 , CHBr3 NaOH(D) (b) H 2 Pd - CaCO 3 , CHBr3 NaOH(D) (c) Na liq.NH 3 , CHCl 3 NaOH (d) H 2 Pd - CaCO 3 , CHCl 3 NaOH O 33. CH2 ¾KB¾O¾r2H® (A) + CHBr3 ¯ O CO2H CO–2 (d) CH3 Product (A) of the reaction is : (c) CO2– CO2H CO2H C – CH3 || (a) (b) CO2H O https://t.me/studyzee

503 34. CN NO2 ¾(¾1()2¾H) OH¾-O(-1¾,mBro¾2l¾e) ® (A); Product (A) is : CO–2 NO2 NH2 Br (a) (b) (c) (d) NO2 NH2 NO2 NO2 O 35. NH ¾N¾aO¾¾Cl ® ( X ) ; Product X will be : H2O (80%) NO2 O CO2H NH2 (a) (b) NH2 CO2H NO2 NO2 CO2H (d) NH2 (c) NO2 CO2H CO2H NO2 36. CH 3 — CH 2 — CH 2 — CH 2 — CH 3 ¾¾CH¾2N¾2 ¾D ® Products Which of the following product(s) is/are can be obtained in the above reaction. (a) Isopentane (b) 3-Methyl hexane (c) n-Pentane (d) 3-Methyl pentane O 37. CH3—C—NH2 KOBr (A) Relation between ( A) & (B) is : LiAlH4 (B) (a) Identical (b) Functional isomer (c) Homologous (d) Positional isomers https://t.me/studyzee

504 38. If we use pyrene (CCl 4 ) in the Riemer-Tiemann reaction in place of chloroform, the product formed is : (a) Salicylaldehyde (b) Phenolphthalein (c) Salicylic acid (d) Cyclohexanol 39. When ethyl amine is heated with chloroform and alcoholic KOH, a compound with offensive smell is obtained. This compound is : (a) A secondary amine (b) An isocyanide (c) A cyanide (d) An acid 40. Which of the following species would not be involved in the Hoffmann rearrangement shown below ? O NH2 ¾B¾r2,¾Na¾OH¾, H2¾O ® NH2 O (a) NHBr O (b) N—s Br (c) N==C==O (d) All of the above are involved in the reaction. 41. In which of the following reactions migration of alkyl group from carbon to oxygen is observed ? (a) Pinacol-pinacolone rearrangement (b) Bayer-villiger oxidation. (c) Prepration of phenol from cumene hydroperoxide. (d) Both (b) & (c) ANSWERS — LEVEL 1 1. (b) 2. (b) 3. (c) 4. (b) 5. (a) 6. (d) 7. (c) 8. (b) 9. (c) 10. (b) 11. (a) 12. (a) 13. (b) 14. (c) 15. (a) 16. (b) 17. (d) 18. (a) 19. (d) 20. (a) 21. (c) 22. (a) 23. (b) 24. (b) 25. (a) 26. (a) 27. (c) 28. (c) 29. (a) 30. (b) 31. (a) 32. (b) 33. (c) 34. (c) 35. (b) 36. (d) 37. (c) 38. (c) 39. (b) 40. (d) 41. (d) https://t.me/studyzee

505 Level - 2 1. Comprehension Hoffmann bromamide reaction involves conversion of a carboxylic acid amide into an amine with a loss of a carbon atom on treatment with aqueous sodium hypobromite. Thus Hoffmann result in shortening of a carbon chain. O R || ¾N¾BaOr¾2¾H ® R - NH 2 + NaBr + Na 2CO 3 - C- NH 2 Mechanism of the reaction is : O O– R – C – NH2 NaOH R – C = NH + Br — Br Na2CO3 + R–NH2 H2O O = C= N–R O R – C – NH – Br – HO O R – C – N –– Br A. Number of moles of NaOH consumed in above reaction. (a) 1 (b) 2 (c) 3 (d) 4 O B. C – NH2 ¾B¾¾r2 ® ( A) ; Product (A) : KOH (Major) (a) Ph - NH 2 (b) Ph - CH 2 - NH 2 (c) Ph - NH - CH 3 (d) Ph – N CH3 CH3 C. Which of the following will not give Hoffmann bromamide reaction. O O || (b) C – NH – Br (a) CH 3 - C - NH 2 OO (c) C – NH2 (d) C – NH – CH3 https://t.me/studyzee

506 O D. NH ¾K¾OB¾r ®( A), Product (A) is : O NH2 (b) NH — CH3 (c) NH2 (d) None of these (a) OK OH NH2 O O 2. Comprehension Given is mechanism of Beckmann rearrangement. C == N H+ C == N CH3 — C == N — CH3 (I) (II) H2O (III) O CH3 OH O—H CH3 — C == N — H (IV) CH3 — C — NH — Ph OH A. Rate determining step in Beckmann rearrangement : (a) I (b) II (c) III (d) IV CH3 C == N B. OH Ph On treatment H 2SO 4 followed by hydrolysis in acidic medium above compound gives. (a) CH 3 - CO 2H, Ph - NH 2 (b) CH 3 - NH 2 ,Ph - CO 2H (c) Ph - CH 2 - NH 2 + Ph - CO 2H (d) Ph - CO 2H + CH 3 - CO 2H C. Which of the following reagent cannot used in Beckmann rearrangement ? (a) TsOH (b) R - SO 2Cl (c) BF3 (d) Ph - Li OH C == N D. ¾P¾C¾l5 ®( A); D CH3 Product ( A) of the above reaction is : https://t.me/studyzee

(a) O O 507 (c) CH3 C — NH (b) C — NH CH3 CH3 CH3 (d) CH3 O C — NH O C — NH 3. Match the column I and II. Column (I) Column (II) Cl (a) ¾a¾q. ¾KO¾H ®( A) ¾H¾¾+ ® (B) ¾C¾HC¾¾l3 ®(C) (p) D.B.E. = even for product (Double bond equivalent) D KOH OH (q) D.B.E. = odd for product (b) ¾H¾¾+ ® ( A) ¾C¾HC¾¾l3 ®(B) D KOH (c) ¾C¾HC¾¾l3 ®( A) ¾C¾HC¾¾l3 ®(B) (r) Ring expansion takes place KOH KOH (d) N OH ¾H¾¾+ ® ( A) ¾C¾HF¾ClB¾r ®(B) (s) Carbene will formed D D | H https://t.me/studyzee

508 Column (II) 4. Match the column I and II. (p) Reimer Tiemann reaction Column (I) (q) Reimer Tiemann expansion (or) Abnormal RNT reaction (a) ¾C¾KHO¾CHl¾3 ® OH (b) ¾C¾KHO¾CHl¾3 ® (c) ¾C¾Cl¾3CO¾ON¾a ® (r) Simman-smith reaction. (s) Increase in carbon takes place D OH (d) ¾C¾H¾2I2¾+Z¾n ® D 5. Match the column I and II. Column (I) Column (II) (a) CO2H ¾S¾OC¾¾l2 ® ¾ ¾NH¾3 ® (p) Aromatic compound will formed ¾ ¾KO¾B¾r ® ¾ ¾HN¾O¾2 ® N C || | N Migration take place from carbon to (b) C C Cl (q) electron deficient nitrogen (A) hv (c) f - CHCl2 ¾ ¾t-B¾uO¾QK¾¾Å ®( A) (r) Carbene will formed in this reaction ¾ ¾f-C¾ºC¾-¾f®(B) ¾ ¾AlC¾l¾3 ®(C ) O2N NO2 (s) N2 will evolve. (d) O || C – NH2¾ ¾KO¾B¾r ® https://t.me/studyzee

509 6. Match the column I and II: Column (I) Column (II) Reaction Intermediate (a) CHCl 3 + KOH ¾¾® (p) Carbocation D (q) Carbanion (b) Br ¾ P¾h-¾¾Li ® (r) Free radical Br D Cl O | || (c) Cl – C – C – OH¾ N¾¾a ® | D Cl OH (d) ¾H¾¾+ ® (s) Carbene D 7. Matrix : Column (II) Column (I) Product Reaction F (a) ¾C¾H¾C¾l3 ® (p) KOH, D Cl (b) ¾C¾H¾FCl¾B¾r ® (q) KOH, D Br (c) ¾C¾H¾Cl2¾B¾r ® (r) KOH, D (d) ¾C¾H¾Br2¾Cl ® (s) KOH, D https://t.me/studyzee

510 8. Comprehension 1. Consider the given reaction for preparation of alkyne. (Fritsch reaction). H dQ Q Cl ¾r¾.d¾.s® Ph–C º C – Ph Ph C = C Cl Ph–Li (Acid-base) C=C Ph Anti group will migrate because of less steric hindrance. 14 H C=C ÅQ A. Br ¾K¾OC¾(C¾H3¾¾)3 ® ( A) ; Major product (A) is : D (major) Br (a) 14 Br (b) 14 Br CºC CºC (c) Ph – C º C14 – Ph (d) Ph – C º C – Ph H Å QC(CH 3)3 C+ B. Br + K O ¾¾®( A), product (A) is : D (a) (b) (c) (d) C. Rate of reaction when the halide ion: (b) IQ > Br Q > Cl Q > F Q (a) IQ > Cl Q > Br Q > F Q (d) F Q > Br Q > Cl Q > IQ (c) F Q > Cl Q > Br Q > IQ D. CH3O C* H (a) CH3O ¾t¾-B¾uO¾K ® (A) (Major) , Product (A) is : (C* = C14) Br D * Br CH3O * (b) Br https://t.me/studyzee

511 CH3O * (d) CH3O (c) * Br Br 9. Comprehension Wolff rearrangement When a-Diazoketones are photo-irradiated or heated at high temperature or reacted with silver oxide or silver salts at room temperature, they loose nitrogen and rearrange to form ketene. The ketenes reacts rapidly with water, alcohol and amines. Therefore, the reactions called Wolff-rearrangement. O || C – CHN2 ¾A¾g2¾O ® N2 + Ph – CH = C = O | | CH 3 - NH 2 ¯ H 2O ¯ Ph - CH 2 - CO 2H Ph - CH 2 - C - NH - CH 3 || O O || ¾A¾g2¾O ®( A. Ph - C- CHN 2 A), Product (A) is : H2O 14 14 14 (a) Ph - CH 2 - CO 2H (b) Ph - CH 2 - CO 2H 14 (c) Ph - CO 2H (d) Ph - CO 2H O Q ÅN *N B. ¾C¾H3¾O¾H ® ( A) (Major), Product (A) is : hv (C* = 14 C) O OCH3 O || * * C – OCH3 (a) (b) O || C – OCH3 * (c) (d) https://t.me/studyzee

512 O H || C. CH3 C – C – CHN2 + CH 3OH ¾A¾g2¾O ® Major product of the reaction is : Et O || Et O H || (a) CH3 C – C – OCH3 (b) CH3 C – C – OCH3 H Et CH3 O (d) None of these (c) H || C – C – OCH3 Et O || C – CHN2 D. ¾A¾g2¾O ®( A) (Major) , Product (A) is : NH3 C – CHN2 || O O O || || C – NH2 CH2 – C – NH2 (a) (b) C – NH2 CH2– C – NH2 || || O O O CH2 – CONH2 || C – NH2 (c) (d) C – NH2 CH2 – CONH2 || O N2 || E. Ph - C - CH 2OCH 3 ¾¾®( A) 90% , product (A) is : D (a) Ph – CH = CH – OH (b) Ph – CH = CH – OCH 3 (c) CH 3 – CH = CH – O – PH (d) CH 3 – CH = CH – OH F. hv ( A) , Product (A) is : O ¾C¾H3¾O¾H ® N2 https://t.me/studyzee

513 (a) (b) O CO2CH3 (c) (d) CO2CH3 CO2CH3 O O || ¾A¾g2¾O ® G. HO - CH 2 - CH 2 - CH 2 - C - CHN 2 ( A) , Product (A) is : D OOO O O (b) O O OO (a) (c) (d) ANSWERS — LEVEL 2 1. A – d, ; B – a; C – d, ; D – a, 2. A – b; B – b; C – d; D – b 3. a – p, r, s; b – q, r, s; c – q, r, s; d – p, r, s 4. a – q, s; b – p, s; c – s; d – r, s 5. a – p, q, s; b ® p, r, s ; c – p, r ; d – p,q 6. a – q, s; b – q, s; c – q, s; d – p 7. a – q; b – p; c – q; d – q 8. A – a; B – c; C – b; D – b 9. A – b; B – c; C – d; D – b; E – b; F – b; G – c https://t.me/studyzee

514 12 AROMATIC COMPOUNDS Level - 1 1. O C || NH – C – CH3 CH3 A B Identify the position where electrophilic aromatic substitution (EAS) is most favourable. (a) A (b) B (c) C (d) A and C NO2 Cl CH3 2. (a) (b) (c) (d) Correct order of rate of EAS (electrophilic aromatic substitution) is : (a) c > b > a > d (b) c > d > a > b (c) a > b > c > d (d) c > d > b > a https://t.me/studyzee

515 NN 3. + Ar — N ºº N Å Cl - ¾® N = N - Ar Above (C—N) coupling reaction take place at : (a) low pH (b) Intermediate pH (c) high pH (d) any pH 4. Which of the following has the lowest heat of combustion ? (a) (b) (c) (d) 5. The product obtained from the reaction is : Br CH2Cl + NaCN ethanol (a) Br CH2CN (b) Br CH2Cl (c) NC CH2CN (d) Br CH2Cl CN CO 6. + O ¾1¾. A¾lC¾l3 ® A ¾Z¾n—¾H¾g, H¾Cl,¾he¾at ® B ¾1¾2..SAO¾lCCl¾l32 ® C. CO 2. H3O+ 3. H3O+ The end product (C) is : O (a) (b) O O O O C C — C6H5 (d) (c) COOH C — C6H5 O https://t.me/studyzee

516 7. How many benzylic hydrogens are present in the hydrocarbon shown below ? (a) 3 (b) 4 (c) 5 (d) 6 (e) 8 8. The major product formed in the reaction is : + HNO3 conc. H2SO4 NO2 NO2 (a) (b) (c) (d) NO2 NO2 9. The major product formed in the reaction is : O ¾C¾on¾c. H¾NO¾3 /¾co¾nc.¾H2S¾O¾4 ® C–O (mononitration) (a) O (b) O2N O O2N C–O C–O OO (c) C – O (d) C – O NO2 NO2 10. Increasing order of rate of reaction with HNO 3 H 2SO 4 is : OO O OO OO O OO OO (i) (ii) (iii) (d) i < ii < iii (a) iii < ii< i (b) ii < iii < i (c) i < iii < ii https://t.me/studyzee

517 11. Increasing order of rate of reaction with Br2 AlCl 3is : OH OH O OH O (i) (ii) (iii) (iv) (a) iii < i < ii < iv (b) iv < ii < i < iii (c) ii < iv < iii < i (d) iv < ii < iii < i 12. Increasing order of equilibrium constant for the formation of a hydrate is : O OO O H3CO CH3O O2N (i) (ii) (iii) (iv) (a) i < ii < iii < iv (b) iv < ii < i < iii (c) ii < iv < iii < i (d) iv < ii < iii < i 13. Rank the following reactions A, B and C in order of increasing rate, Me Me Me Me SO3/H2SO4 SO3H (A) SO3/H2SO4 (B) NO2 SO3H NO2 (C) SO3/H2SO4 SO3H (a) B > A > C (b) B > C > A (c) A > B > C (d) A > C > B 14. Rank in order of increasing rate of reaction towards EAS with bromine in the presence of FeBr 3 . (A) (B) (C) (a) B < A < C (b) B < C < A (c) A < B < C (d) A < C < B 15. Identify the position where E.A.S. can take place. (a) 1 (b) 2 (c) 3 (d) 4 https://t.me/studyzee

518 16. ¾¾H¾+ ®( A) ¾¾HN¾O¾3 ®(B). DD Product (B) in the above reactions is: (b) NO2 NO2 (a) (c) (d) NO2 NO2 1 2 O Sulphonation is most favourable at the carbon number... . 17. 3 NH 4 (a) 1 (b) 2 (c) 3 (d) 4 18. Arrange the following in decreasing order of reactivity towards EAS (electrophilic aromatic substitution) CH3 CD3 CT3 (a) (b) (c) a > c > b (c) (a) a > b > c (b) c > b > a (d) c > a > b 19. (a) (b) (c) (d) Decreasing order of rate of electrophilic aromatic substitution is : (a) a > b > c > d (b) a > c > b > d (c) b > a > c > d (d) b > c > a > d https://t.me/studyzee

20. Arrange the following in increasing order of rate of Nitration: 519 Me D NO2 Cl DD (a) (b) DD (a) b < c < a < d < e D (c) d < a = c < e < b (c) (d) (e) Me HH (b) d < e < a = c < b 21. (d) a < c < b < e < d Me Me HD DD (a) (b) (c) The rate of nitration will be: (d) c > a > b (a) a > b > c (b) a > c > b (c) a = b = c 22. The major product of the reaction is (a) CH3 – C ¾1¾. C¾H3¾COC¾l/A¾lC¾l3 ® Product. O 2. H2O O ||C CH3 (b) (c) (d) C C O CH3 O CH3 || || 23. Arrange in their decreasing order of rate of electrophilic aromatic substitution : (i) (ii) (iii) (a) i > ii > iii (b) iii > ii > i (c) iii > i > ii (d) i > iii > ii https://t.me/studyzee

520 Cl Cl 24. + HO - ¾® ( A) ; Product (A) of the given reaction is : Cl (4 mole) (major) Cl Cl (2 mole) Cl O Cl Cl O Cl (a) O (b) O Cl Cl Cl Cl Cl Cl Cl Cl O O (c) (d) O O Cl Cl Cl Cl 25. In which of the following compound electrophilic aromatic substitution take place in phenyl ring present in left hand side ? OO (a) C — O (b) C — NH O (c) CH2 — O (d) CH2 — C 26. + A ¾¾H2S¾O¾4 ® ; Reactant (A) is : O | (c) O CO2H (a) O (d) CO2H (b) O O | 27. Which of the following compounds is the slowest to react with nitrosonium ion (NO + ) ? O CH3 OMe (a) (b) (c) (d) https://t.me/studyzee

521 OO || || NaCN 28. ¾(¾CH¾3 )2¾CH¾–C¾– ¾Cl ® ¾C¾lem¾m¾ens¾e¾n ® ¾C¾H ¾3–C¾– ¾Cl ®¾ ¾ ¾Red¾P +¾H¾I ®(Ibuprofen) ¾H2S¾O¾4 ® AlCl3 reduction AlCl3 H 3O Å Ibuprofen is : CH3 (a) CH 3 — CH 2 | CH — CO 2H (b) CH 3 — CH — CH 2 CH — CO 2H | | CH3 CH3 COOH CH3 – CH - CH3 (c) (d) O 29. CH2 - C AlCl3 O CH2 - CH - C O What is the major product of above Friedel-Craft reaction ? OO CO2H (a) (b) CO2H O CO2H O (c) (d) CO2H 30. What combination of acid chloride or anhydride and arene would you choose to prepare given compound ? C — CH2 — CH2 — CO2H O https://t.me/studyzee

522 OO AlCl3 (a) + Cl — C — CH2 — CH — C — Cl CH3 O (b) + AlCl3 O O O + O AlCl3 (c) O O + AlCl3 (d) O 31. In the given conversion best yield will obtained with : O C (A) CH3 (B) O O || (a) A = CH 3 — C — Cl, AlCl 3 , B = Zn(Hg), HCl O || (b) A = Zn(Hg),HCl, B = CH 3 — C — Cl, AlCl 3 (c) A = CH 3 — CH 2 — Cl, AlCl 3, B = Zn(Hg), HCl (d) A = NH 2 — NH 2 HO - ,D , B = CH 3 — CH 2 — Cl, AlCl 3 https://t.me/studyzee

523 32. Rank the following in order of decreasing rate of reaction with alkoxide ion (CH 3CH 2O - ) in a nucleophilic aromatic substitution reaction : Br Br Br Br NO2 NO2 NO2 NO2 NO2 NO2 12 34 (a) 3 > 4 > 1 > 2 (b) 3 > 4 > 2 > 1 (c) 2 > 1 > 4 > 3 (d) 4 > 3 > 2 > 1 33. Identify the principal organic product of the following reaction. F O2N Br+ NaSCH 3 ¾® product (a) F (b) SCH3 CH3S Br O2N Br CH3S F F (c) Br (d) SCH3 O2N O2N 34. Which position will be attacked most rapidly by the nitronium ion (–NO 2 )+ when the compound undergoes nitration with HNO 3 H 2SO 4 : O AB CD OCH3 (a) A (b) B (c) C (d) D NH2 35. ¾C¾on¾c.H¾2SO¾¾4 ®( X ) ¾¾Br2¾H2¾O ®(Y ): Product (Y) of this reaction is : excess NH2 NH2 Br SO3H Br Br (a) (b) Br SO3H https://t.me/studyzee

524 NH2 NH2 Br Br Br Br (c) (d) SO3H Br Br 36. All the hydrocarbons shown are very weak acids. One, however, is far more acidic than the others. Which one is the strongest acid ? (a) (b) (c) (d) O 2. SOCl2 4. MeOH 37. + O 1. AlCl3 (A) 3. NaN3 (B) 5. LiAlH4 (C) 6. NaH, (D) 7. CF3 Cl 8. D O CF3 Product (D) in above sequence is : CF3 OO (a) NH — CH3 (b) CH3 OH OH N — CH3 (d) NH (c) CF3 38. The action of bromine water (excess) on salicylic acid results in the formation of : Br COOH Br COOH (b) OH (a) Br OH Br Br Br COOH (c) OH (d) Br Br Br https://t.me/studyzee

525 39. What is the correct order of o p ratio when E + attacks the following system ? PhF PhCl PhBr PhI A B CD (a) A < B < C < D (b) A = B = C = D (c) D < C < B < A (d) D < B < A < C 40. How many products are capable of beings formed from toluene in each of following reaction ? CH3 HNHO(2S43O0°4) Mono-nitration (A) HNO3 (H82H0S°N)OO43 Di-nitration (B) H2SO4 (110°) Tri-nitration (C) (a) A = 3,B = 6,C = 8 (b) A = 3,B = 6,C = 6 (c) A = 3,B = 6,C = 10 (d) A = 3,B = 4,C = 6 41. Nitration takes place at the which position of the given compound ? CMe3 DA C CHMe2 B (b) B (a) A (d) D (c) C 42. CH2 — CO2H Ac2O ? , Indentify the product. (a) CO2H D (c) CH2 — CO2H CH2 — CCl2Ac (b) CO2H CO2Ac O O O (d) O O O https://t.me/studyzee

526 Cl AlCl3 (A) ; Unknown (A) is : O 43. Cl – C C=O O || (a) (b) C = O (c) (d) Ph -C -Ph C=O Cl Cl | Cl 44. + H2SO4 ( A) (1) NBS ( B) RCO3H ( C) . Product (C) is : (a) O O D (2) alc. KOH (d) (b) OH O (c) OH Ph Ph 45. The reaction of toluene with chlorine in the presence of light gives : Cl CH3 CH3 CH2Cl CH3 (a) Cl Cl (c) (b) (d) 46. Cl O AlCl3 (A) NH2 – NH2 Cl (a) + Cl H2O HO– , D (B), Product (B) in this reaction is : 47. (b) (c) CH2 – OH (d) OH + HF D Suitable product of this reaction is : (a) (b) (c) (d) https://t.me/studyzee

527 Me NaSH 48. A; Product (A) of the reaction is : Cl (b) no reaction CH2 – SH SH SH (c) (d) (a) CH3 Cl Cl NH2 49. Br2 (A) (i) NaNO2/HCl ( B) , Product (B) in this reaction is : H2O (ii) H3PO2 Br Br Br Br Br Br Br (b) (c) Br (a) (d) Br Br Cl 50. 2 Na2S (A), Product (A) in this reaction is : NO2 NO2 Cl (a) SH S (d) SH (b) S (c) NO2 NO2 NO2 NO2 NH2 O–H 51. NaNO2/HCl (A) (B), Product (B) of this reaction is : (mild basic medium) (Major) CH3 https://t.me/studyzee

528 OH CH3 (b) (a) N == N - Ph N == N CH3 OH OH (c) (d) CH3 N == N Ph O–H 52. HNO3/H2SO4 (A) + ( B) (more volatile) (less volatile) Product (A) of the above reaction is : OH OH OH NO2 NO2 (c) (d) (b) (a) NO2 NO2 NH2 53. 2ICl x + 2HCl; Major product ( x) in this reaction is : NO2 (56 – 63%) NH2 I NH2 NH2 NH2 I (a) (b) I I I I I I (c) NO2 (d) NO2 NO2 NO2 NO2 54. HNO3 , van’t-Hoff factor (i) for this reaction is : (a) 2 H2SO4 (b) 3 (c) 4 (d) 5 NH2 ? NO2 55. , the missing reagent is : (a) CF3CO 3H (b) H 2SO 4 (c) LAH (d) NaBH 4 https://t.me/studyzee

529 X OCH3 56. CH3O– NO2 NO2 above reaction is an example of Nucleophilic aromatic substitution. Which of the following halide (-X) is most readily replaced. (a) – F (b) – Cl (c) – Br (d) – I 57. When comparing the hydrogenation of benzene with that of a hypothetical 1, 3, 5-cyclohexatriene, benzene ________ than the cyclohexatriene. (a) absorbs 152 kJ /mol more heat (b) gives off 152 kJ/mol more heat (c) absorbs 152kJ /mol less heat (d) gives off 152 kJ/mol less heat 58. Which of the following hydrogens is most easily abstracted on reaction with bromine free radicals, Br• ? CH3CH2 CH3 (a) (b) (c) (d) (a) a (b) b (c) c (d) d 59. The electrophilic aromatic substitution proceeds through a : (a) free radical (b) sigma complex (c) benzyne (d) carbene 60. Which of the following substitution of benzene is ortho-para in electrophilic substitution and ortho-para in nucleophilic substitution ? (a) – NO 2 (b) – NO (c) – SO 3H (d) – SO 2Me 61. The number of possible isomers of dichloronitrobenzene is : (a) 3 (b) 4 (c) 6 (d) 8 62. Which of the following is not an aromatic compound ? (a) (b) (c) (d) 63. Consider the following sequence of reactions. COOH ¾¾1.¾SO¾Cl¾2 ® ¾C¾oZnn¾c-.HH¾gCl® B A 2. anhyd. AlCl3 CH2C6H5 The end product (B) is: CHO O CH2C6H5 (a) (b) (c) (d) https://t.me/studyzee

530 NO2 64. Ph - NO 2 + Et - Cl ¾¾AlC¾l3 ®( A), Product (A) of the given reaction is : NO2 (a) Ph – NH – Et (b) no–reaction (c) (d) Et Et 65. In nitration of benzene by mixed acid the rate of reaction will be : (a) C 6H 6 = C 6D 6 = C 6T6 (b) C 6H 6 > C 6D 6 > C 6T6 (c)NCH62H 6 = C 6D 6 > C 6T6 (d) C 6H 6 < C 6D 6 < C 6T6 66. H2SO5 (A) Ph – CH2CN (B) ; Product (B) is : EtO–/D (a) Ph - N = C -CN (b) Ph - N = C - Ph | Ph (c) Ph - N = N - Ph (d) Ph - CH = CH - Ph 67. Which of the following ring compounds obeys Huckel's rule ? (a) C 4H -1 (b) C 4H +1 (c) C 4H -2 (d) C 4H 4 4 4 4 68. Nitration of which of the following reactant gives maximum % of meta product (using HNO 3 H 2SO 4) ? (b) Aniline (a) Toluene (c) Benzene (d) Isopropyl benzene Br Ph Ph 69. ¾¾2Ag¾BF¾4 ® ( x) 2BF4- ; compound (x) will be : Ph Ph Br Ph Ph Ph Ph Ph Ph Ph Ph (a) +2 (b) –2 (c) +1 (d) –1 Ph Ph Ph Ph Ph Ph Ph Ph O- (1) CO2 70. (A) (2) HÅ Which of the following is true statement about the reaction ? (a) Ortho isomer is major if PhONa is used (b) Para isomer is major if PhOK is used (c) Product formed is further used for preparation of drug aspirin (d) All of these https://t.me/studyzee

531 71. Two benzyne intermediates are likely to be formed equally. Reaction with amide ion can occur in two different directions with each benzyne, giving three possible products. They are formed in a 1 : 2 : 1 ratio. Asterisk (*) refers to 14 C. * Cl NaNH2 (A) Product major; product ( A) is : NH3 NH2 * * * NH2 (a) (b) NH2 (c) NH2 (d) * 72. Which one of the following undergoes nucleophilic aromatic substitution at the fastest rate ? Cl Cl Cl Cl (a) (b) (c) (d) NO2 Cl CH3 OCH3 Br 73. For the reaction ; ? ¾¾® ; the best combination of reactants is : NO2 (a) C 6H 5Br + HNO 3 , H 2SO 4 (b) C 6H 5Br + H 2SO 4, heat (c) C 6H 5NO 2 + Br2 , FeBr3 (d) C 6H 5NO 2 + HBr 74. The action of AlCl 3 in Friedel Craft’s reaction is: (a) to absorb HCl (b) to release HCl (c) to produce electrophile (d) to produce nucleophile 75. n-Butylbenzene on oxidation with hot alkanine KMnO 4 gives : (a) benzoic acid (b) butanoic acid (c) benzyl alcohol (d) benzaldehyde 76. Which sequence of steps describes the best synthesis of 2-phenylpropene ? (a) Benzene + 2-chloropropene , AlCl 3 (b) 1. Benzaldehyde (C 6H 5CH = O) + CH 3CH 2MgBr, diethyl ether 2. H 3O + 3. H 2SO 4, heat (c) 1. Bromobenzene + Mg, diethyl ether 2. Propanal (CH 3CH 2CH = O) 3. H 3O + 4. H 2SO 4, heat (d) 1. Bromobenzene + Mg, diethyl ether 2. Acetone [(CH 3 )2 C = O] 3. H 3O + 4. H 2SO 4, heat 77. What are the products of the following reaction ? OCH2CH2OH excess HBr heat (a) Br OCH2CH2Br (b) Br + BrCH2CH2OH (c) OH + BrCH2CH2Br (d) Br + BrCH2CH2Br https://t.me/studyzee

532 78. What is the product obtained by heating the following allylic ether of phenol ? OCH2CH = CHC6H5 OH OH C|6H5 CHCH = CH2 CH2CH = CHC6H5 (a) (b) OC6H5 (d) HO C|2H5 CH2CH = CH2 CHCH = CH2 (c) 79. When you ingest aspirin, it passes through your stomach, which has an acidic pH, before traveling through the basic environment of your intestine. Provide the structure form as it exists in the intestine. O O O – C – CH3 OH O – C – CH3 O- O CO2H (b) CO2CH3 (c) CO-2 (d) C – OH (a) 80. Which of the following sets of reagents, used in the order shown, would be enable for the preparation of p-chlorophenol from p-chloronitrobenzene ? (a) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2 , H 2SO 4 ; 4. H 3PO 2 (b) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2 , H 2SO 4 ; 4. H 2O, heat (c) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2, H 2SO 4 ; 4. ethanol (d) 1. NaOH, heat ; 2. HCl 81. Which one of the following compounds undergoes bromination of its aromatic ring (electrophilic aromatic substitution) at the fastest rate ? (a) (b) (c) (d) NH OH O N NH 82. H O || ¾C¾H3¾-C¾-¾Cl ®(P) ¾¾Anh¾y. A¾lC¾l3 ®(Q). Product (Q) in this reaction is : D O O – Me OCOMe C – Me OMe (a) (b) (c) (d) OH OH https://t.me/studyzee

NO2 533 NO2 83. ¾C¾CHH3¾O3OH¾–,¾D ® (P) ; The product (P) will be : Cl (major) Cl NO2 NO2 OCH3 (a) (b) (c) (d) 84. Cl Cl OCH3 Cl OCH3 OCH3 Cl OCH3 NaNO2, CH2 – N – CH2 HCl, 90°C (A) ; Product (A) is : | CH2 (a) Ph - CH 2 -N - CH 2 - Ph (b) Ph - CH 2 -N -N == O | | N=O Ph CH2 – Ph (c) Ph – CH2 – N (d) Ph – N = O | CH2 – Ph N N=O N NH2 N || | 85. + NaNO2 + HCl H | NH2 This reaction is example of : (a) Intermolecular C – N coupling (b) Intramolecular C – N coupling (c) Intermolecular N – N coupling (d) Intramolecular N – N coupling 86. The total number of isomeric trimethylbenzene is : (a) 2 (b) 3 (c) 4 (d) 6 87. Caliene, C7H 6, is expected to be a fairly polar aromatic molecule. Which of the following resonance forms contributes to the greatest extent towards the real structure (resonance hybrid) of the molecule ? + :– –1 (a) (b) (c) (d) Å https://t.me/studyzee

534 88. Which of the following molecules is expected to have the greatest resonance stabilization ? (a) (b) (c) (d) 89. In the reaction given below, the major product formed is : O N Br2(1 mole) Product. Fe Br O O (a) N (b) N Br OO (c) N (d) N Br Br 90. p-aminophenol reacts with one equivalent of acetyl chloride in the presence of pyridine to give mainly : OH O OH OH OCOCH3 C – CH3 (a) (b) (c) (d) NH2 NH2 C – CH3 NHCOCH3 NH2 O 91. Which of the following reactions can be used to prepare acetophenone ? ¾1¾. A¾lC¾l3 ® (a) C6H 6 + CH 3 COCl (b (C 6H 5COO)2 Ca + (CH 3COO)2 Ca ¾¾he¾at ® 2. H2O (c) C 6H 6CN ¾1¾. C¾H3¾M¾gI® (d) All of these 2. H3O+ 92. Consider the following sequence of reactions. C 6H6 + CH3CH = CH2 ¾H¾h3eP¾aO¾t 4 ® A ¾2¾.1H.¾O3O2,+¾h, eha¾et¾at ® B + C The products (B) and (C) are : (a) benzaldehyde and acetaldehyde (b) benzoic acid and acetic acid (c) phenol and propionaldehyde (d) phenol and acetone 93. An organic compound having the molecular formula C 8H10O on being heated with I2 and dilute NaOH gives a yellow precipitate. The expected compound is : (a) C 6H 5CH 2CH 2OH (b) CH3 CH2OH https://t.me/studyzee

535 (c) H3C OH (d) CHOHCH3 CH3 94. The product (B) of the reaction sequence is : Cl CH2Br ¾M¾g.¾Et¾2O ® A ¾1¾. C¾H3C¾H¾O ® B. OH | 2. H3O+ (a) CH3CH (b) Cl OH | CH2Br CH2CHCH3 (c) CH2C|H CH2C|HCH3 (d) CH2=CH CH2Br OH OH 95. Consider the following sequence of reactions. ¾ ¾Os¾O 4¾® A ¾ ¾ 1. ¾HIO¾4 ¾¾® B. The final product (B) is : NaHSO 3 ¾ 2. NaOH, heat CH3 COOH CH2CHO COOH COOH (a) (b) (c) (d) O COCH3 COCH3 96. For the reaction, the product expected is : O O ¾1¾. M¾eM¾gB¾r (2¾m¾ol¾e) ® product, O O 2. H 3O + O Me OH (a) O (b) Me OH Me OH O OH (c) O C CH3 Me Me (d) CH3 C OH O https://t.me/studyzee

536 97. Hydrogenation of naphthalene (P) with excess hydrogen gas stops cleanly at 1, 2, 3, 4-tetrahydronaphthalene (Q). What conclusion can be drawn from this experiment ? excess H2 Pd — C (cat.) (P) (Q) (a) the hydrogenation of P is exothermic (b) one aromatic ring of P is more reactive than the aromatic ring of Q (c) one aromatic ring of P is less reactive than the other ring of Q (d) reduction of the first C = C of P is faster than reduction of the second or third C = C 98. Suggest the best reaction conditions for the synthesis shown below. NO2 Br (a) (1) HNO 3 , H 2SO 2; then (2) Br2 (b) (1) Br2; then (2) HNO 3 , H 2SO 2 (c) (1) CH 3Br, AlBr3 ; then (2) HNO 3 , H 2SO 3 (d) HNO 3 , H 2SO 2, then (2) Br2 , FeBr3 99. Cl In the above compound Cl will liberated easily in the form of : (a) Cl Å (b) Cl - (c) Cl · (d) Cl 2+ 100. Consider the following sequence of reactions: PhCO 2H ¾1¾. P¾C¾l5 ® A ¾1¾. P¾4O1¾0. ¾he¾at ® B. The final product (B) is : 2. NH3 2. H2 Ni (a) benzonitrile (b) benzylamine (c) aniline (d) benzamide 101. The major product of the acetylation of salicylic acid with Ac 2O H + followed by heating with anhydrous AlCl 3 is : COOH COOH OH OH (a) O (b) O https://t.me/studyzee

537 COOH O COOH OH (d) OH (c) O 102. Which one of the following statements is True: 103. 12 (a) PhLi adds to both compounds with equal ease (b) PhLi does not add to either of the compounds (c) PhLi reacts readily with 1 but does not add to 2 (d) PhLi reacts readily with 2 but does not add to 1 The major product expected from the mono-bromination of phenyl benzoate is : Br Br (a) COO (b) COO (c) Br COO (d) COO Br 104. The Birch reduction of benzoic acid gives : (a) COOH (b) COOH (c) COOH (d) COOH 105. The decreasing order of reactivity of meta-nitrobromobenzene (I), 2,4,6-trinitrobromo- 106. benzene (II), para-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV) towards HO - ions is : (a) I > II > III > IV (b) II > IV > III > I (c) IV > II > III > I (d) II > IV > I > III Which of the following tetracarboxylic acid form di-anhydride : COOH COOH COOH COOH (a) COOH (b) COOH COOH COOH (c) neither (a) nor (b) (d) both (a) and (b) https://t.me/studyzee

538 ¾2¾I-¾Cl ® (A); unknown (A) is : CO2H OH 107. O C—I CO2H CO2H I CO2H I OH OH OH (a) (b) (c) (d) I Cl Cl I I 108. Ph – NH 2 + Ph 3COH ¾ H¾+ ¾D ® P (not a N-derivative), Product (P) is : (major) NH2 NH2 NH2 CPh3 CPh3 (a) (b) (c) (d) CPh3 109. Deduce structure of (A). CPh3 (A) C 8H10 ¾K¾M¾nO¾4 ®(B) C8H 6O 4 ¾ B¾¾r2 ® C 8H 5BrO 4(C ) (one-product only) : Fe (a) (b) (c) (d) 110. The deamination of Ph 2C(OH)CH 2NH 2 with NaNO 2 - HCl gives a product (P), which on 111. oxidation gives benzoic acid only. Identify the product (P). (a) Ph - CH 2 - CH 2 - Ph O || OO (b) Ph - C -CH 2 - Ph || || (c) Ph - C - C -Ph (d) Ph - CH 2 - NH - Ph Ph - CO 2H ¾S¾OC¾¾l2 ® A ¾M¾e2¾N¾H ® B ¾(¾C¾) ® Ph - CHO, unknown reagent (C) is : (a) LiAlH 4 (b) NaBH 4 (c) LiAlH(t -BuO)3 (d) PCC CH 2Cl 2 https://t.me/studyzee

539 CH2CH3 O NH2 — NH2, NaOH CH2CH3 triethylene glycol. heat CH3 — C — Cl 112. AlCl3 (A) (B) (80%) (73%) CH2CH3 Product (B) is : (a) (b) (c) (d) O || ¾A¾lC¾l3 ® ( A) ¾K¾M¾nO4¾,¾D ®(B) 113. C 6H 5(CH 2 ) 5 C - Cl CS 2 C12H14O H 3Or ; Compound (B) is : CO2H (a) (b) C — (CH2)4 — CO2H O O CO2H C (c) (d) O CO2H C RR O R 114. HNO3 NO2 H2SO4 + (ortho) NO2 In the above reaction o/p ratio will be highest when : (a) R = - CH 3 (b) R = - CH 2 - CH 3 (c) R = - CHMe 2 (d) R = - CMe 3 https://t.me/studyzee

540 CO2H 115. ¾H¾N¾O¾3 ® (1) ¾ ¾Ba¾se¾® (2) ¾S¾OC¾¾l2 ® (3) ¾(¾1) ¾Et2¾N¾H ®(4) n -PrCl (2) H2 Pd HO product (4) in the above reaction is : OO NO2 C — N — Et NH2 C — N — Et (a) Et (b) Et O O O NO2 O NH2 C — NEt2 C — NH — Et (d) (c) O O Cl 116. Br Cl (A); Product (A) of the reaction is : Br AlCl3 (c) (d) Br (a) Br H (b) H 117. Ph - CHO + 2 ¾H¾2S¾O¾4 ® major product of this reaction is : (a) Ph 3CH OH (c) (d) Ph 2CH 2 | Ph Ph (b) Ph -C -Ph | Ph 118. NH2 Cl (A); Product (A) of this reaction is : Br (a) N — H(b) (c) (d) Cl N N || HH https://t.me/studyzee

541 NO2 119. ¾H¾NO¾3+¾H2¾SO¾4 ® (X); Compound (X) is : five days NO2 to complete (a) 1,2,4-Trinitrobenzene (b) 1,3,5-Trinitrobenzene (c) 1,2,3 -Trinitrobenzene (d) Tri-nitro toluene (TNT) 120. O O ¾(¾ii()i)¾SHOC¾Cl¾l2 ®( A) ¾PA¾hl-C¾l3H®(B) ¾K¾OH¾M¾eO¾H ® (C); Compound (C) is : OO || (a) Ph — CH2 — C — (b) Ph - CH = CH -C -CH 3 OO || (c) Ph — C — (d) Ph -C -CH = CH - CH 3 O 121. O ¾CA¾6lCH¾l36 ®( A) ¾(¾ii) ¾H(2i¾)PPdC¾-lB5a¾SO¾4 ®(B) ¾N¾H¾2-N¾H¾2 ®(C); Compound (C) is : H Ph O C == N C == N (b) (a) CH == N CH == N CH == CH — Ph (d) C == N (c) CH == N Ph OH 122. ¾(¾i) a¾q N¾aH¾CO¾3 b¾o¾il ® ( A) , Product (A) in this reaction is : H 3O + OH (major) OH OH OH (a) (b) (c) (d) No reaction OH OH OH CHO CO2H OH https://t.me/studyzee

542 iv 123. NO2 I , Identify position where attack of (ArO- ) is favourable. i iii (c) iii (d) iv ii (a) i ¾C¾¾l2 ®( A), Product (A) of this reaction is : (b) ii 124. S— S NO2 NO2 SH NO2 NO2 SH (b) S — Cl (d) (a) NO2 (c) NO2 NO2 O C — Me 125. ¾¾HN¾O¾3 ® (A) ¾Z¾n(¾H¾g) ® (B), Product (B) of this reaction is : H 2SO 4 HCl CH2 — Me CH2 — Me O C — Me CH2 — Me NO2 (a) (b) (c) (d) Me NO2 NH2 NO2 126. +HN = CH - Cl ¾A¾lC¾l3 ®( A) ¾H¾3O¾+ ®(B), Product (B) of this reaction is : Me CH3 (a) (b) (c) No-reaction (d) O C — Me CHO CH2CO2H CHO 127. ¾E¾tO¾H ® ¾(¾i) N¾a¾H ® ¾(¾i()iiN)¾aHO+¾H ® ¾(¾i) S¾OC¾l2 ® ; Product H+ (ii) MeI (ii) AlCl3 End product of the above reaction is : https://t.me/studyzee

543 O Me (a) (b) O O O (c) (d) 128. Å– Ph - NH 2 ¾C¾H3¾-C¾l (2¾mo¾l¾e) ®(A) ¾P¾h-¾N2¾Cl ® (B) (major) Butter yellow Product of the above reaction is : Me N Me Me — N — Me N == N — Ph (a) (b) Me — N — Me N == N — Ph Me Me — N — N == N — Ph (c) (d) N == N — Ph 129. p-Toluedine reacts with benzene diazonium chloride to form compound, which on boiling with aq. H 2SO4 give ......... products : (a) 3 (b) 2 (c) 4 (d) 5 NO2 130. ¾ a¾q N¾H¾3 ®( A) ¾ H¾B2r¾O2 ® ( B) ¾(¾i)N¾aN¾O2+¾H¾Cl ® (C ) (ii) H3PO2 Cl Product (C) of the above reaction is : NO2 NO2 NO2 NO2 Br Br (a) Br (b) (c) Br (d) Br Br Br Br https://t.me/studyzee

544 131. Fe+2 ( A) ¾B¾¾r2 ® (B) ; Major product (B) of this reaction is : (a) ¾H¾2O¾2 ® H 2O (ºº 100%) (Fenton's reagent) OH OH CH OH Br Br Br (b) (c) (d) Br Br Br Br 132. NO2 ¾H¾O¾– ® (A) ; Product of the given reaction is : Br NO2 OH Br NO2 (a) (b) OH Br HO Br Br (c) NO2 NO2 (d) HO Br NH2 133. ¾(¾CH¾3CO¾)2¾O ®( A) ¾H¾N¾O¾3 ® ( B) ¾ H¾H2¾+O ® (C ), Product (C) of this reaction is : H 2SO 4 NH2 NH2 NO2 NO2 (a) (b) (c) (d) NO2 NO2 NO2 NO2 https://t.me/studyzee

545 NO2 134. ¾B¾r2¾(2m¾ol¾e) ®( A) (major) ; Product (A) will be : (a) Fe NO2 NO2 NO2 NO2 Br Br Br (d) (b) (c) Br Br Br Br Br 135. ¾ (i) ¾HN¾O¾3 ® ( A) ¾K¾M¾nO4¾¾D ®(B) ¾S¾OC¾¾l2 ®(C); Product (C) of this reaction is : (a) ¾ (ii) H2SO4 (Di- nitro product) COCl O C — Cl NO2 NO2 NO2 NO2 (b) (c) (d) NO2 NO2 NO2 NO2 Cl 136. ¾C¾H3¾—¾NH¾—C¾H¾3 ®( A) ¾H¾F¾Cel ®(B) ; Product (B) of this reaction is : NO2 CH3 N CH3 CH3 N CH3 (a) (b) NH2 NH2 (d) None of these CH3 N CH3 NH2 (c) https://t.me/studyzee

546 OH NH2 137. (A) ¾ ¾(i)S¾OC¾l2 ®(B) ¾B¾r2+¾K¾O¾H ® (ii) NH3 Which of the following compound on hydrolysis gives reactant (A) : OO (a) C — O (b) C — O NO2 HO HO NO2 OO (c) NO2 C—O (d) C—O NO2 NO2 OH 138. ¾H¾N¾O3 ¾H2¾SO¾4 ® (A); MeO Product (A) of the above reaction is : NO2 NO2 (b) NO2 MeO (a) MeO NO2 (d) (c) MeO MeO Me O 139. N ¾¾B¾r2 ® ; Product of the reaction is : | H CS 2 Br (a) O O NH (b) — Br CH 2 O NH CH2 — Br (c) NH (d) O NH Br https://t.me/studyzee

OH OO 547 O 140. H2 (A) (B) ; Product (B) of this reaction is : Pd OH (Paracetamol) NO2 O O — C — CH3 OH O NH2 C — CH3 (a) (b) (c) (d) NH2 HN NH2 OH O O 141. + O ¾2¾.2¾eqAul¾Civla3¾len¾ts ® ( A) ¾Z¾n(¾H¾g) ®(B) ¾H¾3P¾O¾4 ®(C) ; HCl O (succinic anhydride) Product (C) of the above reaction is : OH O O OH (a) (b) (c) (d) O 142. + C ¾A¾lC¾l3 ® Product; O 82% yield H Product of the above Friedel-Craft reaction is : (a) CO2H O C CO2H (c) (b) (d) https://t.me/studyzee

548 143. Which of the following 2-halo nitrobenzene is most reactive towards nucleophilic aromatic substitution ? F Cl Br I NO2 NO2 NO2 NO2 (a) (b) (c) (d) 144. Choose the best method to prepare given compound : CH3 CH3 CH3 NO2 (a) ¾(¾1)H¾NO¾3+¾H2¾SO¾4 ® (b) ¾(¾1) ¾Me¾3CC¾l A¾lC¾l3 ® (c) (2) Me3CCl AlCl3 (2) HNO3 H2SO4 CH3 CH3 (d) ¾(¾2)C¾H(13¾)-HC|¾NHO-¾3CHH¾22-SC¾Ol 4A¾lC¾l3 ® | CH3 ¾(¾1) ¾CH¾3 —¾CH¾— C¾H2¾—¾Cl/¾AlC¾¾l3 ® (2) HNO3 H2SO4 145. ¾H¾H2NS¾OO¾34 ® ( A) ¾ P¾Hd,¾2C ® (B) ¾ K¾M¾nO¾4 ®(C ) ¾ E¾tO¾H ® ( D) (Para isomer) H+ Benzocaine Benzocaine has been used as a component of appetite suppressants, burn and sunburn remedies. Benzocaine is : O (a) CO2Et CO2Et C NH OEt (b) (c) C (d) 146. NH2 (a) O — CH3 O OH NH2 NH2 Br OH ¾H¾B¾r ®( A) ; Product (A) of this reaction is : OCH2 — Br CH D 86% OCH3 OH (b) (c) (d) Br OH https://t.me/studyzee

OCH3 549 OCH3 OH O—I 147. ¾H¾I(¾exc¾es¾s) ® Product. D (d) OCH3 OH Predict major product of the above reaction is : OH I CH3 (a) OH I OH (b) (c) OH I 148. ¾H¾N¾O¾2 ® (A) (Major) ; Product (A) is : OH (a) HNO 3 (d) NO2 OH OH NO2 Cl NO2 (b) (c) NO 149. Arrange in their decreasing order of rate in SNAr. Cl Cl Cl Cl NO2 NO2 NO2 NO2 (ii) NO2 (iv) NO2 (i) (iii) (v) (a) i > ii > iv > iii > v (b) ii > i > iii > v > iv (c) v > iii > i > ii > iv (d) v > iii > ii > i > iv 150. Which one of the following compounds undergoes bromination of its aromatic ring (electrophilic aromatic substitution) at the fastest rate ? (a) (b) N (c) NH H (d) NH O https://t.me/studyzee