Route Maps Reactions

Question 1

alkene → haloalkane

Answer 1

FREE RADICAL SUBSTIUTION/ HALOGENATION

alkene + halide ions → haloalkane

Question 2

alkene → alcohol

Answer 2

ELECTROPHILLIC ADDITION
alkene + water → alcohol
HP04, 300C, 65atm

Question 3

alcohol → alkene

Answer 3

ELIMINATION/ DEHYDRATION
alcohol → alkene + water
strong acid, 170C

Question 4

haloalkane → alcohol

Answer 4

ALKALINE HYDROLYSIS/ NUCLEOPHILLIC SUBSTITUTION
haloalkane + OH- → alcohol + halide ions
water, NaOH, reflux

Question 5

alcohol → haloalkane

Answer 5

HALOGENATION
alcohol + halide ions → haloalkane + water
NaX, H2SO4, reflux

Question 6

haloalkane → nitrile

Answer 6

NUCLEOPHILLIC SUBSTITUION
haloalkane + ethanol + NaCN ==> nitrile + halide ions
reflux

Question 7

nitrile functional group

Answer 7

C≡N

Question 8

hydroxynitrile functional group

Answer 8

OH
/
C-C≡N

Question 9

nitrile → amine

Answer 9

REDUCTION
nitrile + [H] → amine
LiAlH4, 150C, Ni catalyst & high pressure

Question 10

haloalkane → amine

Answer 10

NUCLEPHILLIC SUBSTITUTION
haloalkane + NH3 → amine + NH4+ X-
heat, ethanol

Question 11

1 amide functional group

Answer 11

O
 //
C-N-H
     /
    H

Question 12

2 amide functional group

Answer 12

O
  //
-C-N-
     /
    H

Question 13

acid anhydride functional group

Answer 13

O
\ /  \ /
 C  C
 //   //
O  O

Question 14

ketone → hydroxynitrile

Answer 14

NUCLEOPHILIC ADDITION

ketone + HCN → hydroxyitrile

Question 15

hydroxynitrile → amine

Answer 15

REDUCTION
hydroxynitrile +[H] → amine
LiAlH4 & dilute acid
Na, ethanol & reflux
Ni catalyst. high temperature and high pressure

Question 16

nitrile → carboxylic acid

Answer 16

ACID HYDROLYSIS/ NUCLEOPHILLIC ADDITION
nitrile + HCl + water → carboxylic acid + NH4Cl
reflux, heat, strong acid catalyst

Question 17

acid anhydride → ester

Answer 17

ESTERFICATION
acid anhydride + alcohol → ester + carboxylic acid
heat

Question 18

amide → carboxylate

Answer 18

ALKALINE HYDROLYSIS
2 amide + NaOH → 1 amide + carboxylate
100C. NaOH

Question 19

acyl chloride → secondary amide

Answer 19

NUCLEOPHILLIC ADDITION

acyl chloride + primary amide → secondary amide + HCl

Question 20

acyl chloride → primary amide

Answer 20

NUCLEOPHILLIC ADDITION

acyl chloride + NH3 → amide + NH4Cl

Question 21

primary amide → carboxylic acid

Answer 21

ACID HYDROLYSIS
amide + water + H+ → 2 amino acids with NH3
acid

Question 22

ester → carboxylate

Answer 22

NEUTRALISATION
ester + NaOH → carboxylate + alcohol
reflux

Question 23

ester → carboxylic acid

Answer 23

ACID HYDROLYSIS
ester + water → carboxylic acid + alcohol
heat, reflux, HCl

Question 24

carboxylic acid → acyl chloride

Answer 24

CHLORINATION

carboxylic acid + SOCl2 → acyl chloride + SO2 + HCl

Question 25

acyl chloride → carboxylic acid

Answer 25

NUCLEOPHILLIC ADDITION/ HYDROLYSIS | acyl chloride + H2O → carboxylic acid + HCl

Question 26

aldehyde → alcohol

Answer 26

REDUCTION aldehyde + [H] → alcohol NaBH4 & heat

Question 27

benzene → nitrobenzene

Answer 27

NITRATION/ ELECTROPHILLIC SUBSITUTION benzene + NO2+ → nitrobenzene + H+ HNO3, H2SO4

Question 28

benzene → alkylbenzene

Answer 28

ALKYLATION/ ELECTROPHILLIC SUBSITUTION benzene + CH3+ → methylbenzene + H+ AlCl3, chloroalkane

Question 29

benzene → acyl benzene

Answer 29

ACYLATION/ ELECTROPHILLIC SUNSITUTION carbonyl group + benzene → acyl benzene + H+ AlCl3, chlorocarbonyl

Question 30

benzene → chlorobenzene

Answer 30

CHLORINATION/ ELECTROPHILLIC SUBSITUTION Cl + + benzene → chlorobenzene + H+ AlCl3, Cl2, FeCl3

Question 31

benzene → bromobenzene

Answer 31

BROMINATION/ ELECTROPHILLIC SUNSITUTION Br + + benzene → bromobenzene + H+ Br2, FeBr3

Question 32

nitrobenzene → aminobenzene

Answer 32

REDUCTION nitrobenzene + [H] → aminobenzene + H2O Sn, reflux, conc HCl

Question 33

aminobenzene → tribromo aminobenzene

Answer 33

BROMINATION/ ELECTROPHILLIC SUNSITUTION Br+ + aminobenzene → tribromo aminobenzene + H+ Br2, FeBr3

Question 34

acyl benzene → hydroxybenzene

Answer 34

HYDROLYSIS/ REDUCTION ketone + [H] → alcohol H2O, NaBH4

Question 35

phenol → bromophenol

Answer 35

BROMINATION | 3Br2 + phenol → tribromophenol + 3HBr

Question 36

phenol → salt

Answer 36

NEUTRALISATION | NaOH + phenol → salt + H2O

Question 37

phenol → nitrophenol

Answer 37

NITRATION | HNO3 + phenol → nitrophenol + H2O