ACS enolate review

Question 1

Which of the following have an enol form?

Answer 1

2-chloropronal

Question 2

Which one of the following has two different enol forms?

Answer 2

3,3-dimethylcyclohexone

Question 3

How many alpha hydrogen are there on 2,4-dimethyl-3-pentanone?

Answer 3

Two

Question 4

Identify the most acid hydrogen for the following compound

Answer 4

2

Question 5

Identify the keto form of the following enol

Answer 5

E- 3-penten-2-one

Question 6

What is the relationship between keto & enol?

Answer 6

constitutional isomers

Question 7

Which of the following has the highest percentage of enol in a keto-enol equilibrium?

Answer 7

2,4-hexanediol

Question 8

What is the adol product of proponal?

Answer 8

3-hydroxy-2-methylpentanal

Question 9

How many different adol products can be formed in the reaction of equal amounts of proponal and butanal with aqueous sodium hydroxide at 0C?

Answer 9

Four

Question 10

Benzalactone is the crossed adol condensation product between benzaldehyde and aceton. Which of the following is the structure of benzalacetone?

Answer 10

C₆H₅CH=CHC^=OCH₃

Question 11

What is the product of the following intramolecular adol condensation reaction?

Answer 11

The with cyclopentene & aldehyde

Question 12

Identify the starting reagent needed to make the following compound by a mixed adol condensation

Answer 12

Benzaldehyde & 3-pentanone

Question 13

The robinson annulation reaction is shown below. identify the missing reagent in the first step

Answer 13

H₂C=CHC^=OCH₃

Question 14

Which one of the following reagents adds a methyl group by conjugate (1,4-addition) addition to an alpha beta unsaturated ketone or aldehyde?

Answer 14

LiCu(CH₃)₂

Question 15

What is the product of the sequence below

Answer 15

3-ethyl-2-methyl-1-hexonal

Question 16

Heating a mixture of 1,3-diphenylacetone and acrolein in trimethyl gives a product C₁₈H₁₆O in 53%yield. The mechanism for the product formation is a micheal addition followed by an intramolecular adol condensation. Whic of the following is the product of this reaction?

Answer 16

The one with Ph on both sides of the carbonyl & a double where ph is on the alpa position of the double bond

Question 17

Identify the following keto form of the following enol structure

Answer 17

2-methylcyclopentanone

Question 18

Which of the following is the mixed adol condensation product of the reaction shown below?

Answer 18

C₆H₅C^=OCH=CHC₆H₅

Question 19

Which of the following cannot form an enolate anion?

Answer 19

2,2-dimethylbutanal

Question 20

Which of the following is the adol addition product of butanal?2-ethyl-3-hydroxyhexenal

Answer 20

2-ethyl-3-hydroxyhexanal