Functional Group 4

Question 1

Oxidation of primary alcohols (synthesis of aldehydes)

Answer 1

R-CH2OH -K2Cr2O7,H2SO4-> RCHO

Question 2

Ozonolysis of Alkenes (synthesis of aldehydes)

Answer 2

RCH=CHR -O3,(CH3)2S-> RCHO + R’CHO

Question 3

Gatterman-Koch formylation (synthesis of aldehydes)

Answer 3

HCl + CO + Ar-H -AlCl3-> Ar-CHO

EX: toluene -> p-methyl benzaldehyde

Question 4

Hydroboration-oxidation of alkynes (synthesis of aldehydes)

Answer 4

R-C=-CR -1.)BH3,2.)THF,H2O2,NaOH-> 2RCHO

Question 5

Reduction of acyl chlorides (synthesis of aldehydes)

Answer 5

R-COCl -H2/Pd/BaSO4-> RCHO

Question 6

Hydration (reaction of aldehydes)

Answer 6

RCHO RCH(OH)2

Question 7

Addition of Grignard reagent (reaction of aldehydes)

Answer 7

RCHO + R’MgX -> R’RCHOH

2dary alcohol

Question 8

Reduction (reaction of aldehydes)

Answer 8

RCHO -LiAlH4,acid-> RCH2OH

Primary alcohol

Question 9

Synthesis of cyanohydrins (reaction of aldehydes)

Answer 9

RCHO -HCN-> RCHCNOH

cyanohydrin

Question 10

Synthesis of imines

Answer 10

RCHO -H2NR’,-H2O-> RCHNR’

Imine/Schiff base

Question 11

Synthesis of oximes (reaction of aldehydes)

Answer 11

RCHO + H2NOH -> R-(CN-OH)-H

Question 12

Synthesis of acetals (reaction of aldehydes)

Answer 12

RCHO + 2R’OH RCH(OR’)2

Question 13

Oxidation (reaction of aldehydes)

Answer 13

RCHO -KMnO4-> RCOOH

Carboxylic acid

Question 14

Clemmensen reduction (reaction of aldehydes)

Answer 14

RCHO -Zn(Hg),HCl-> RCH3

Alkane

Question 15

Oxidation of secondary alcohols (synthesis of ketones)

Answer 15

R-CHOH-R’ -K2Cr2O7,H2SO4-> RCOR’

Question 16

Acylation of arenes (synthesis of ketones)

Answer 16

1.) RCClO -AlCl3-> R(C+)O (acylonium ion)
2.) R(C+)O + benzene ->
R(CO)-benzene

Question 17

Ozonolysis of Alkenes (synthesis of ketones)

Answer 17

RCH=CR’R” -O3,(CH3)2S-> RCHO + R’CHR”

Question 18

Synthesis of organolithium and carboxylic acid (synthesis of ketones)

Answer 18

RCOOH + 2R’Li -> RCR’(OLi)2

-H+-> RCOR’

Question 19

Synthesis from nitriles (synthesis of ketones)

Answer 19

RCN + R’MgX -> R(CNMgX)R’

-H+,H2O-> RCOR’

Question 20

Hydration (reaction of ketones)

Answer 20

RCOR’ RC(OH2)2R’

Hydrate

Question 21

Addition of Grignard (reagent reaction of ketones)

Answer 21

RCOR’ + R”MgX -> R(COMgX)R’R” -H+-> R(COH)R’R”

tertiary alcohol

Question 22

Reduction (reaction of ketones)

Answer 22

RCOR’ -LiAlH4-> R(COH)HR’

2ndary alcohol

Question 23

Synthesis of cyanohydrins (reaction of ketones)

Answer 23

RCOR’ -HCN-> R(HOCCN)R’

Cyanohydrin)

Question 24

Synthesis of imines (reaction of ketones)

Answer 24

RCOR’ -H2NR”-> R(CNR”)R’

Imine/Schiff base

Question 25

Synthesis of oximes (reaction of ketones)

Answer 25

RCOR’ + H2NOH -> R(CNOH)R’

Oxime

Question 26

Clemmensen reduction (reaction of ketones)

Answer 26

RCOR’ -Zn(Hg),HCl-> RCH2R’