Test III (Reagents)

Question 1

Acid-catalyzed hydrolysis of esters

Answer 1

Water
Acid (eg. HCl)

Question 2

Acid hydrolysis of amides

Answer 2

Water
Acid (eg HCl)

Question 3

Base hydrolysis of amides

Answer 3

Water
Base (eg NaOH)

Question 4

Acid hydrolysis of nitriles

Answer 4

Water
Acid (eg HCl)

Question 5

Base hydrolysis of nitriles

Answer 5

Water
Base (eg NaOH)

Question 6

Acid Chloride + ____ -> Amide

Answer 6

Amine (eg NH3) OR R-NH2

Question 7

Acid Chloride + ____ -> Ester

Answer 7

Alcohol (eg MeOH) OR R-OH

Question 8

Acid Chloride + ____ -> Anhydride

Answer 8

Carboxylic acid

Question 9

Anhydride + ____ -> Amide

Answer 9

Amine (eg NH3) OR R-NH2

Question 10

Anhydride + ____ -> Ester

Answer 10

Alcohol (eg MeOH) OR R-OH

Question 11

Reduction of esters (to primary alcohol)

Answer 11

Lithium aluminum hydride (LiAlH4) (H connects to middle)

Question 12

Reduction of amides (to primary amines)

Answer 12

Lithium aluminum hydride (LiAlH4) (H connects to middle)

Question 13

Reduction of nitriles (RCN) to primary amine

Answer 13

Lithium aluminum hydride (LiAlH4) (H connects to C)

Question 14

Reduction of esters with Grignard reagents

Answer 14

Grignard reagent (eg. MeMgBr or PhMgBr)

Question 15

Acid catalyzed bromination of α position

Answer 15

Br2
Acid (eg HCl)

Question 16

Basic bromination of α position

Answer 16

Br2
Base (eg NaOH)

Question 17

Bromination of α position of carboxylic acid

Answer 17

Br2
PBr3

Question 18

Base-catalyzed aldol reaction

Answer 18

Base (eg NaOH)

Question 19

Base-catalyzed cross aldol reaction

Answer 19

Base (eg. NaOH)
Additional carbonyl compound

Question 20

Base aldol condensation + Heat + ____ -> α-β unsaturated carbonyl

Answer 20

Base (eg. NaOH)

Question 21

Base cross aldol condensation + Heat + ____ -> α-β unsaturated carbonyl

Answer 21

Base (eg. NaOH)
Additional carbonyl compound

Question 22

Acid-catalyzed aldol condensation + ____ -> α-β unsaturated carbonyl

Answer 22

Acid (eg. HCl)

Question 23

Acid-catalyzed aldol cross condensation + ____ -> α-β unsaturated carbonyl

Answer 23

Acid (HCl)
Additional carbonyl compound

Question 24

Claisen condensation

Answer 24

Base (eg NaOH)

Question 25

Cross Claisen condensation

Answer 25

Base (eg NaOH) Additional carbonyl compound

Question 26

Alkylation of malonates with alkyl bromide

Answer 26

Alkyl bromide Base (eg NaOH)

Question 27

Knoevenagel condensation (aldol condensation of malonate with aldehyde)

Answer 27

Aldehyde Base (eg NaOH)

Question 28

Conjugate addition with ___ produces a β-nitrile carbonyl compound

Answer 28

Potassium cyanide

Question 29

Conjugate addition with ____ produces a β-amino carbonyl compound

Answer 29

Amine

Question 30

Basic conjugate addition of enolate/enol

Answer 30

Enolate

Question 31

Acidic conjugate addition of enolate/enol

Answer 31

Enol

Question 32

Direct addition (multiple options)

Answer 32

NaBH4 OR LiAlH4 (adds H) OR R-Li (eg Me-Li) (adds R/Me) OR -CN (reversible, adds -CN)

Question 33

Conjugate addition

Answer 33

R2CuLi (eg MeCuLi, Mg2CuLi) (adds R/ME) OR -CN (adds CN)