Latest organic mind maps with answers 2020

SYNTHESIS CHAPTER 5: CHEMICAL REACTIONS CC HYDROCARBONS FREE RADICAL SUBSTITUTIONS: R-X (ALKANES) R-X H2 , Pt/ Pd/ Ni, X2 , ∆ uv + HX GENERAL REACTION MECHANISM: Mg, ALKANES ether CC R-MgX H2O, HH H3O+ @ H+ R-X Na, dry ½(3n+1)O2 nCO2 + ether (excess) (n+1)H2O + heat R-COONa NaOH ½(2n+1)O2 nCO + (limited) (n+1)H2O + [email protected] heat

SYNTHESIS CHAPTER 5: CHEMICAL REACTIONS HYDROCARBONS SAYTZEFF’S RULE: CC Major product is the alkene which have greater (ALKENES) HH number of R (alkyl) groups. H2 , Pt/ Pd/ Ni, ∆ H2SO4 (conc), ∆ X2 , ELIMINATION REACTIONS CCl4, CC CC ELECTROPHILIC ADDITION REACTIONSALKENESdarkXX H OH CC X2 , CC CC KOH, alcohol, H2O X OH HX reflux HX OXIDATION OF ALKENES: CC M HX CC + MnO2 KMnO4 , HBr , (brown ppt) OH−, cold, dilute ROOR (BASIC @H2O2 CC OH OH OXIDATION – H Br BAEYER’S TEST) observation: AM purple turn to brown KMnO4 , H3O+, hot, conc. C O+ O C (ACIDIC H2O, H+ CC OXIDATION) H3O+ @ 3 TYPES OF H OH M PRODUCTS: H2SO4 (conc), ∆ 1. KETONE + KETONE CC 2. KETONE + C.A 3. KETONE + CO2 + H2O H OSO3H M H2O, ∆ C O+ O C O3, CC H2O, H+, 3 TYPES OF Zn H OH PRODUCTS: 1. KETONE + KETONE MARKOVNIKOV’S RULE: ANTI MARKOVNIKOV’S RULE: 2. KETONE + ALDEHYDE H atom should be attached H atom should be attached to ch3e.mA@LDtaEmHYhDidEi+.USIM to the C that bonded to the C that bonded to LESS H ALDEHYDE GREATER H atom atom [email protected]

SYNTHESIS CHAPTER 6: CHEMICAL REA AROMATIC ELECTROPHILIC SUB COONa COMPOUNDS NaOH , X2 , ∆ Fe@ Al @FeX3 @AlX3 ARENE HNO3 (conc.), H2SO4 (conc.), Δ Zn(s), Δ R-X , OH Fe@ Al @FeX3 @AlX3 RCOCl , AlCl3, Δ [email protected]

ACTIONS CHEMICAL REACTIONS OF ALKYL BENZE3NE BSTITUTION CH2-Cl X X2 , uv NO2 CH3 R X2 , X Fe@ Al O @FeX3 + CH3 C-CH3 @AlX3 X COOH KMnO4 , H+, Δ

SYNTHESIS CHAPTER 7: HALOALKANES CC HH KCN, CC Ethan CC X2 , UV HX HALOALKANES KOH( HBr, ROOR NaOH X2, CCl4 RX NH3 Etha R OH PCl3@ PCl5@ Na, PBr3 @ SOCl2 Mg, dry [email protected] KO eth ref

CHEMICAL REACTIONS 4 nol, reflux R CN LiAlH4, ether, CH2NH2 RH3O+@H2, Ni, ∆ R OH NUCLEOPHILIC SUBSTITUTION RH2SO4, ∆@ COOH (aq), reflux @ H2O@H+ H(aq), reflux 3, If excess anol, ∆ NH3 is used R NH2 R NH2 ether R R' NOT R' excess NH NH3 R , R MgX NOT R' ether excess N R'' NH3 R OH, CC ELIMINATION hanol, flux

FURTHER REACTION OF GRIGNARD REAGENT CHAPTER 7: HALOALKANES HALOALKANES Mg, dry ether GRIGNARD REAGENT R-X R MgX [email protected]

ALKANES 5 H2O,H+ RH O 1° ROH H HC H RCH H2O,H+ OH X O 2° ROH R R CH H2O,H+ RCH OH O 3° ROH RC R' R H2O,H+ RCR OH O=C=O, CARBOXYLIC ACID H2O,H+ R COOH

SYNTHESIS CHAPTER 8: Na HYDROXY C6H12O6 COMPOUNDS NaO Enzyme R H2O, H+ ALCOHOL H+, ∆ CC R-OH O RC R-X KOH(aq), RO – H CLEAVAGE reflux@ H+, NaOH(aq), KMnO4 reflux K2Cr2O7 Mg, dry H PCC ether R C CH3 KMnO4, OH K2Cr2O7 PCC R-MgX Refer to Iodoform further Test KMnO reaction of I2, NaOH K2Cr2O Grignard PCC reagent RO-Na + NaI + H2O + CH3I [email protected]

CHEMICAL REACTIONS 6 a RONa+ + H2 HX R-X OH 2 layers solution forms PBr3 R-Br + HPO3 because aliphatic alcohol O is weaker acid compared R – OH CLEAVAGE PCl3 R-Cl + HPO3 to phenol. PCl5 C OH , SOCl2 R-Cl + POCl3 + O HCl↑ ∆@ R C OR + R-Cl + SO2 + O H2O @ HCl HCl↑ C Cl , ROH 1° ∆ 4,H+, ∆ @ 7, H+, ∆ KMnO4,H+, ∆ @ HCl, R-Cl + H2O K2Cr2O7, H+, ∆ ZnCl2 O RC OH ,H+, ∆ @ ROH 2° ROH 1 : do not turn cloudy 7, H+, ∆ @ ROH 2 : turns cloudy in 5 minutes ROH 3 : turns cloudy immediately O4,H+, ∆ @ No reaction because H2SO4 (conc), O7, H+, ∆ @ there is no H at the 3° ∆ carbon

CHAPTER 8: 7 HYDROXY SYNTHESIS COMPOUNDS CHEMICAL REACTIONS Cumene Process \\\\\\ Na O-Na+ [email protected] + H2 PHENOL NaOH O-Na+ Br2, CCl4 + H2O OH OH Br + HO Br Br2, H2O Br OH ELECTROPHILIC SUBSTITUTION REACTIONS Br HNO3 Br dilute OH NO2 + HO NO2 O2N OH HNO3 NO2 concentrated FeCl3 O2N (yellow) OH FeCl3

CHAPTER 9: SYNTHESIS PCC, CHEMIC CARBONYL CH2Cl2 ALDEHYDE COMPOUNDS ROH 1 O3, Zn O CC H2O, H+, C RH RCOOH OXIDATION Ag + RCOO- + NH4+ +NH3 KMnO4,H+, ∆ @ RCOO- + Cu2O +H2O K2Cr2O7 H+, ∆ RCOO- + Cu2O +H2O *Pinkish purple solution formed TOLLEN’S TEST [Ag (NH3)2]+, OH- FEHLNG’S TEST Cu2+,OH- (Fehling blue soln) BENEDICT’S TEST Cu2+(Benedict solution) SCHIFF REAGENT 2[Ag (NH3)2], CONDENSATION R C O + H2 N Z C N Z + H2O H2N NH2 hydrazine H2N OH hydroxylamine H2N N phenylhydrazine H R H2N N NO2 2,4-dintrophenylhydrazine R (2,4-DNPH) [email protected] O2N

CAL REACTIONS SYNTHESIS 8 KETONE KMnO4,H+, ∆ ROH 2 O @ K2Cr2O7, H+, ∆ @ PCC, CH2Cl2 CC C KMnO4,H+, ∆ HR R' @ K2Cr2O7, H+, ∆ O3, Zn, H2O, H+, O R C Cl , AlCl3 Iodoform O Methyl test R C CH3 carbonyl group observation: I2/NaOH yellow ppt REDUCTION Reagent: NUCLEOPHILIC ADDITION a)LiAlH4@NaBH4 OH in ether, H+ b)Zn, H+, ∆ HCN c)H2, Ni/Pt/Pd, ∆ C CN OH O H2O, C H+ C [R] ROH 1 OH H O [R] ROH 2 ROH 1, ROH 2, ROH 3 C R' *refer to Grignard Reagent mind map

SYNTHESIS CHAPTER 10: CARBOXYLIC ACID R-OH 1° KMnO4, H+, ∆ @ K2Cr2O7 ,H+, ∆ O RCH R CARBOXYLIC R-CN H2O, H+, ∆ RMg-X CO2, H2O, H+ O RO-H, A R C O R + H2O H+ R ESTER ∆ OO R C O C R + H2O ACID ANHYDRIDE [email protected]

CHEMICAL REACTIONS 9 M: RCOOM+ + H2 SUBSTITUTE H WITH METAL Na@K@Mg RCOOM+ + H2O MOH: NaOH @ RCOOM+ + CO2 + H2O KOH C ACID MCO3: ROH 1 REDUCTION Na2CO3 @ MgCO3@ REAGENT: NaHCO3 1. LiAlH4, ether, H3O+ 2. NaBH4 [R] 3. H2(g), Ni/Pt/Pd, heat PCl3 RCOCl + HPO3 ACYL CHLORIDE PCl5 ACYL CHLORIDE SOCl2 RCOCl + POCl3 + HCl↑ AMIDE NH3 RCOCl + SO2 + HCl↑ O RNH2 R-NH-R’ O R C Cl R C NH2 + H2O @ HCl OR R C NH + H2O @ HCl OR R C N R + H2O @ HCl

10 CHAPTER 11: NH3, EtOH, R NH2 RNH3+ Cl AMINES reflux HCl R2NH2 + Cl R-X RNH2 R R3NH+ Cl R NH R-NH-R’ R R NR OR R-CN R-NO2 Reagent: R C NH + HCl a)LiAlH4 in ether, O H3O+ O b)NaBH4 R C NH2 c)Zn, H+, ∆ R C Cl OR d)H2, Ni/Pt/Pd, ∆ R-NH2 RCN R + HCl No reaction O X2, OH-, H2O R C NH2 X2= Cl2 @ Br2 Aniline Br2, Br H2O Br NH2 Br REACTION WITH NITROUS ACID (HONO) Hinsberg's Reagent O 1 aliphatic RNH2 + NaNO2 HCl RCH=CH2 + RCH2CH2Cl + RCH2CH2OH + N2 amine cold S Cl 2 aliphatic Gas is released O amine Benzenesulphonyl chloride R 3 aliphatic (BSC) amine R2NH + NaNO2 HCl R N N O + NaCl + H2O cold 1 aromatic Yellow oil amine 2R3N NaNO2, HCl R3NHCl + R3N N OCl cold Clear solution NH2 N2+Cl NaNO2, HCl + NaCl + H2O HINSBERG’S TEST cold arenediazonium salt No gas is released below 5°C BSC KOH HCl 2 aromatic CH3 NaNO2, HCl CH3 1° Ppt Clear Ppt amine NH N NO formed solution formed below 5 oC N-Methyl-N-nitrosoaniline Yellow oil (yellow oil) Ppt No No formed change change 3 aromatic 2° amine CH3 CH3 [email protected] N NaNO2, HCl O N N CH3 No No Clear change change solution CH3 below 5 oC N,N-Dimethyl-4-nitrosoaniline 3° (precipitate) Yellow ppt