TOOLKIT

Question 1

(ACYL CHLORIDE or anhydride) to PRIMARY AMIDE

Answer 1

acylation

c. NH3, room temp

Question 2

SECONDARY AMIDE (peptide) to CARBOXYLIC ACID

Answer 2

acid hydrolysis

heat under reflux

(alkali hydrolysis produces the salt of the carboxylic acid)

Question 3

ALDEHYDE to CARBOXYLIC ACID

Answer 3

oxidation

heat under reflux with acidified potassium dichromate

Question 4

ALCOHOL to CARBOXYLIC ACID

Answer 4

oxidation

heat under reflux, acidified potassium dichromate

Question 5

ALCOHOL to ALKENE

Answer 5

elimination reaction

concentrated sulfuric acid, heating under reflux

Question 6

AMINE to SECONDARY AMIDE (peptide)

Answer 6

acylation

R-COCl, room temp

Question 7

HALOALKANE to ALCOHOL

Answer 7

nucleophilic substitution

heat under reflux with NaOH

Question 8

(ACYL CHLORIDE or anhydride) to CARBOXYLIC ACID

Answer 8

water hydrolysis

Question 9

ALKENE to ALCOHOL

Answer 9

electrophilic addition

concentrated sulfuric acid then add water

Question 10

HALOALKANE to AMINE

Answer 10

nucleophilic substitution

c. NH3, heat in a sealed tube

Question 11

ALCOHOL to HALOALKANE

Answer 11

nucleophilic substitution

conc. HBr
REFLUX

Question 12

(ACYL CHLORIDE or anhydride) to ESTER

Answer 12

esterification

react with alcohol at room temp

Question 13

ALCOHOL to KETONE

Answer 13

MUST BE SECONDARY ALCOHOL
Oxidation

heat under reflux, acidified potassium dichromate

Question 14

ALCOHOL to ALDEHYDE

Answer 14

MUST BE PRIMARY ALCOHOL
Oxidation

Distill with a limited amount of acidified potassium dichromate

Question 15

ALKANE to HALOALKANE

Answer 15

radical substitution

halogen + sunlight/UV radiation

Question 16

CARBOXYLIC ACID to ESTER

Answer 16

esterification

react with an alcohol with c. sulfuric acid
heat under reflux

Question 17

ALKENE to ALKANE

Answer 17

electrophilic addition

Nickel catalysts, 150 .C 5 atm

Question 18

ALKENE to HALOALKANE

Answer 18

electrophilic addition

HBr at room temp

Question 19

(ACYL CHLORIDE or anhydride) to SECONDARY AMIDE (peptide)

Answer 19

acylation

R-NH2 (amine) at room temp

Question 20

(ACYL CHLORIDE or anhydride) to PHENYL ESTER

Answer 20

esterification

with a phenol, at room temp

Question 21

ESTER to CARBOXYLIC ACID

Answer 21

Hydrolysis

sulfuric acid, heat under reflux

Question 22

BENZENE to BROMOBENZENE

Answer 22

Electrophilic substitution (bromination)
react with Br2
Heat under reflux, FeBr3 catalyst

Question 23

BENZENE to CHLOROBENZENE

Answer 23

Electrophilic substitution (chlorination)
react with Cl2
Room temp, AlCl3 catalyst
anhydrous

Question 24

BENZENE to BENZENESULFONIC ACID

Answer 24

electrophilic substitution (sulfonation)

c. H2SO4
heat under reflux

Question 25

BENZENE to NITROBENZENE

Answer 25

Electrophilic substitution (nitration) c. HNO3 c. H2SO4 catalyst <55°C

Question 26

BENZENE to ALKYL-BENZENE

Answer 26

electrophilic substitution (friedel crafts alkylation) react with R-Cl (R is an alkyl group) heat under reflux, anhydrous conditions

Question 27

BENZENE to ACYL-BENZENE

Answer 27

electrophilic substitution (Friedel-Crafts acylation) AlCl3 Catalyst, heat under reflux, anhydrous conditions react with a R-COCl

Question 28

PHENYLAMINE to DIAZONIUM COMPOUND

Answer 28

Nucleophilic substitution (diazotisation) NaNO2 (NITRITE), HCl <5°C

Question 29

DIAZONIUM COMPOUND to AZO DYE

Answer 29

Electrophilic substitution with a coupling agent <5°C