Ch. 19: Ketones and Aldehydes

Question 1

Hydrate formation reagent

Answer 1

[H+], H2O (reversible the same way)

Question 2

What does hydrate formation do?

Answer 2

=O to 2 -OH groups

Question 3

Acetal formation reagent

Answer 3

[H+], ROH, -H2O

Question 4

What does acetal formation do?

Answer 4

=O to 2 -OR groups

Question 5

Cyclic acetal formation reagent

Answer 5

[H+], HOCH2CH2OH (ethylene glycol), -H2O

Question 6

What does cyclic acetal formation do?

Answer 6

Forms acetal (adds ethylene glycol ring w/out H; “cap”)

Question 7

Cyclic thioacetal formation reagent

Answer 7

[H+], HSCH2CH2SH (ethylene dithiol), -H2O

Question 8

What does cyclic thioacetal formation do?

Answer 8

Forms acetal (adds ethylene dithiol w/out H; “cap”)

Question 9

Desulfurization reagent

Answer 9

Raney Ni (Ra-Ni)

Question 10

What does desulfurization do?

Answer 10

Removes S atoms and replaces with H (can remove acetal cap if applicable)

Question 11

Imine formation reagents

Answer 11

[H+], RNH2, - H2O

Question 12

What does imine formation do?

Answer 12

Replaces O with N-R

Question 13

Enamine formation reagent

Answer 13

[H+], R2NH, -H2O

Question 14

What does enamine formation do?

Answer 14

Replaces O with N-R2

Question 15

Oxime formation reagent

Answer 15

[H+], NH2OH, - H2O

Question 16

What does oxime formation do?

Answer 16

Replaces O with N-OH

Question 17

Hydrazone formation reagent

Answer 17

[H+], NH2NH2, -H2O

Question 18

What does hydrazine formation do?

Answer 18

Replaces O with N-NH2

Question 19

Wolff-Kishner reduction reagent

Answer 19

NaOH, H2O, heat

Question 20

What does wolff-kishner reduction do?

Answer 20

Replaces N-NH2 with H2 (separates DB)

Question 21

Reduction of a ketone reagent

Answer 21

1. LAH 2. H3O+

Question 22

What does reduction of a ketone do?

Answer 22

Reduces ketone to alcohol (=O to
-OH)

Question 23

Grignard reaction reagent

Answer 23

1. RMgBr 2. H3O+

Question 24

What does Grignard reagent do?

Answer 24

Reduces ketone to alcohol with R group as substituent

Question 25

Cyanohydrin formation reagent

Answer 25

KCN, HCl

Question 26

What does cyanohydrin formation do?

Answer 26

Reduces ketone to alcohol with CN group as substituent

Question 27

Wittig reaction reagent

Answer 27

H2C=PPh3

Question 28

What does witting reaction do?

Answer 28

Reduces ketone to alkene (=O to =)

Question 29

Baeyer-villiger oxidation reagent

Answer 29

RCO3H

Question 30

What does Baeyer-villiger oxidation do?

Answer 30

Makes ketone into ester (adds OCH3 to alpha carbon)