Functional Group 5

Question 1

Oxidation of primary alcohols and aldehydes (synthesis of carboxylic acids)

Answer 1

RCH2OH -H2CrO4,KMnO4-> RCOOH

Question 2

Carboxylation of Grignard reagent (synthesis of carboxylic acids)

Answer 2

RX -Mg,ether-> RMgX -CO2-> RCOO-+MgX -H+-> RCOOH

Question 3

Hydrolysis of nitriles (synthesis of carboxylic acids)

Answer 3

RCH2X -NaCN,acetone-> RCH2C=-N -H+(cat),H2O-> RCH2COOH

Question 4

Oxidation of alkylbenzenes (synthesis of carboxylic acids)

Answer 4

Alkylbenzene (with Y pi bonded to ring) -Na2Cr2O7,H2SO4-> a benzoic acid

Question 5

Oxidative cleavage of Alkenes and alkynes (synthesis of carboxylic acids)

Answer 5

RCH=CR’R” -> RCOOH + R’COR”

Carboxylic acid + ketone

Question 6

Conversion to salts (reactions of carboxylic acids)

Answer 6

RCOOH -base-> RCOO^-Y+ + H2O

Ex: acetic acid + ethylamine -> ethylammonium acetate

Question 7

Synthesis of Acid chlorides (reactions of carboxylic acids)

Answer 7

RCOOH + SOCl2 -> RCOCl + SO2 + HCl

Ex: acetic acid + thionyl chloride -> ethanyl chloride + SO2 + HCl

Question 8

Esterification (reactions of carboxylic acids)

Answer 8

RCOOH + R’OH RCOOR’ + H2O (ester)
Or
RCOOH + CH2N2 -> RCOOCH3 + N2 (methyl ester)

Question 9

Synthesis of amides (reactions of carboxylic acids)

Answer 9

RCOCl + R’NH2 -> RCONHR’ + HCl

Question 10

Synthesis of anhydrides (reactions of carboxylic acids)

Answer 10

RCOCl + R’COOH ->

R(C=O)-O-(C=O)-R’ + HCl

Question 11

Synthesis of primary alcohols (reactions of carboxylic acids)

Answer 11

RCOOH -LiAlH4,H2O-> RCH2OH

Primary alcohol

Question 12

Synthesis of ketones (alkylation) (reactions of carboxylic acids)

Answer 12

RCOOH -2RLi,H2O-> RCOR’

Ketone

Question 13

Alkylation (Synthesis of amines)

Primary amine

Answer 13

RCH2X + NH3 -> RCH2NH2

Question 14

Alkylation (Synthesis of amines)

Secondary amine

Answer 14

TNH2 + R’X -> RR’NH

Question 15

Alkylation (Synthesis of amines)

Tertiary amine

Answer 15

3RX + NH3 -> R3N

Question 16

Alkylation (Synthesis of amines)

Quaternary amine

Answer 16

4RX + NH3 -> R4N+

Question 17

Reduction (Synthesis of amines)

Primary amine

Answer 17

1. ) RC=N -LiAlH4-> RCH2NH2
2. ) RCONH2 -LiAlH4-> RCH2NH2
3. ) RCH2N3 -LiAlH4-> RCH2NH2
4. ) RCH2NO2 -LiAlH4-> RCH2NH2

Question 18

Reduction (Synthesis of amines)

Secondary amine derivative

Answer 18

R-N=-C -LiAlH4-> RNHCH3

Question 19

Reduction (Synthesis of amines)

Primary aromatic amine

Answer 19

1. ) ArNO2 + H2 -> ArNH2

2. ) ArNHOH + H2 -> ArNH2

Question 20

Conversion to salts (reaction of amines)

Answer 20

RCH2NH2 + HX -> RCH2NH3+ + X- (ammonium salt)

Question 21

Synthesis of imines (reaction of amines)

Answer 21

RCOR’ + R”NH2 R(CNHR”)OHR’ R(C=NR”)R’ + H2

Imines/Schiff base

Question 22

Synthesis of oximes (reaction of amines)

Answer 22

RCOR’ + HONH2 R(CNHOH)OHR’ R(C=NOH)R’ + H2O

Oxime

Question 23

Alkylation (reaction of amines)

Answer 23

RNH2 + XCH2R’ -> RNHCH2R’ + HX

Salt of secondary amine

Question 24

Acylation (reaction of amines)

Answer 24

RCOCl -R’NH2-> R-(C=O)-NHR’ + HCl

Amide

Question 25

Oxidation of secondary amines (reaction of amines)

Answer 25

RR’NH -H2O2-> RR’NOH + H2O

Secondary hydroxylamine

Question 26

Oxidation of tertiary amines (reaction of amines)

Answer 26

R3N -H2O2-> R3N^+-O^- + H2O

Tertiary amine oxide

Question 27

Diazotization (reaction of amines)

Answer 27

RNH2 -NaNO2,HCl-> [R-N=-N]^+Cl^-

Alkane diazonium salt