Deck 9: Aldehydes and Ketones: Nucleophilic Addition Reactions

Question 1

Instructions: $\alpha$ , $\beta$ -Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the $\beta$ carbon, as shown below. Use this information to answer the following question(s).

-Refer to instructions. Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.

Answer 1

Question 2

Instructions: Draw structures corresponding to each of the following names.
Draw:
cyclohex-2-enone

Answer 2

Question 3

Instructions: Provide IUPAC names for each structure below.
Name:

Answer 3

m-nitrobenzaldehyde or 2-nitrobenzaldehyde

Question 4

Instructions: Predict the products from the information given for the following question(s).
Predict:

Question 5

Instructions: Draw structures corresponding to each of the following names.
Draw:
5,5-dimethylcyclohexane-1,3-dione (dimedone)

Question 6

Instructions: Predict the products from the information given for the following question(s).
Predict:

Question 7

Instructions: Provide IUPAC names for each structure below.
Name:

Question 8

Instructions: Draw structures corresponding to each of the following names.
Draw:
2,2-dimethylcyclopentane-1,3-dione

Question 9

Instructions: Consider the reaction below to answer the following question.
Refer to instructions. Write the complete stepwise mechanism for the reaction shown above. Show all intermediate structures and all electron flow with arrows.

Question 10

Instructions: Consider the data below to answer the following question(s).
Cyanohydrins are important intermediates in the synthesis of $\alpha$ -hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. When a cyanohydrin is treated with aqueous base, however, the original carbonyl compound is isolated.

-Refer to instructions. Identify the electrophile and nucloephile in the reaction of benzaldehyde with hydrogen cyanide.

Question 11

Instructions: Draw structures corresponding to each of the following names.
Draw:
trans-3-isopropylcyclohexanecarbaldehyde

Question 12

Instructions: Provide IUPAC names for each structure below.
Name:

Question 13

Instructions: Consider the data below to answer the following question(s).
Cyanohydrins are important intermediates in the synthesis of $\alpha$ -hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. When a cyanohydrin is treated with aqueous base, however, the original carbonyl compound is isolated.

-Refer to instructions. The reaction of an aldehyde with hydrogen cyanide is an example of _____ reaction.

A) a nucleophilic substitution
B) an electrophilic addition
C) an electrophilic substitution
D) a nucleophilic addition

Question 14

Instructions: Provide IUPAC names for each structure below.
Name:

Question 15

Many nucleophilic addition reactions of aldehydes and ketones are catalyzed by acid or base. Bases catalyze hydration by:

A) making the carbonyl group more electrophilic
B) shifting the equilibrium of the reaction
C) making the carbonyl group less electrophilic
D) converting the water to hydroxide ion, a much better nucleophile

Question 16

Instructions: $\alpha$ , $\beta$ -Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the $\beta$ carbon, as shown below. Use this information to answer the following question(s).

-Refer to instructions. This reaction is called a(n) _____ reaction.

A) conjugate addition.
B) electrophilic addition.
C) direct addition
D) 1,2-addition.

Question 17

Instructions: Consider the reaction below to answer the following question.
Refer to instructions. The electrophile, the nucleophile and the catalyst in this reaction are indicated by letters _____, _____, and _____, respectively.

Question 18

The substance formed in the following reaction is called:

A) vicinal diol
B) geminal diol
C) acetal
D) hydrate
E) b or d

Question 19

Instructions: Draw structures corresponding to each of the following names.
Draw:
benzophenone

Question 20

Instructions: Consider the reaction below to answer the following question.
Refer to instructions. The product of this reaction is called:

A) an ylide
B) an acetal
C) a gem diol
D) a hydrate

Question 21

Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source of carbon.

Question 22

Predict the products of the following reactions.

Question 23

Instructions: Predict the products from the information given for the following question(s).
Predict:

Question 24

Instructions: Predict the products from the information given for the following question(s).
Predict:

Question 25

Instructions: Predict the products from the information given for the following question(s).
Predict:

Question 26

What is the correct structure for 2-hydroxyacetophenone?

A)
B)
C)
D)

Question 27

What is the IUPAC name of the following compound?

A) 3-methyl-3-phenylpropanol
B) 3-phenylbutanal
C) 3-phenyl-1-butanone
D) 3-phenylbutanoic acid

Question 28

Instructions: Predict the products from the information given for the following question(s).
Predict:

Question 29

What hemiacetal would form from the internal nucleophillic addition reaction of the following compound?

Question 30

The nucleophillic addition of water to an aldehyde or ketone

A) is irreversible.
B) dependent on the structure of the carbonyl.
C) favored by neutral conditions.
D) produces a stable tetrahedral product.
E) all of these.

Question 31

Outline the synthetic steps necessary to carry out the conversion below. You may use any organic or inorganic reagents you need. Show the structures of all intermediate compounds that would probably be isolated during the course of your synthesis, and show all necessary reagents.

Question 32

Predict the products of the following reactions.