Deck 9: Aldehydes and Ketones: Nucleophilic Addition Reactions

Question 1

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

Answer 1

Question 2

The substance formed in the following reaction is called:

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

Answer 2

E

Question 3

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

Answer 3

Question 4

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

Question 5

Instructions: Consider the data below to answer the following question(s). Cyanohydrins are important intermediates in the synthesis of a-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 6

Provide IUPAC names for each structure below.
Name:

Question 7

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 8

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 9

Instructions: a,b-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the b 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.

Question 10

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 11

Instructions: a,b-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the b 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 12

Provide IUPAC names for each structure below.
Name:

Question 13

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

Question 14

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

Question 15

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

Question 16

Provide IUPAC names for each structure below.
Name:

Question 17

Provide IUPAC names for each structure below.
Name:

Question 18

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

Question 19

Instructions: Consider the data below to answer the following question(s).
Cyanohydrins are important intermediates in the synthesis of a-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 20

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 21

Predict the products of the following reactions.

Question 22

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

Question 23

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 24

What is the correct structure for 2-hydroxyacetophenone?

Question 25

Predict the products of the following reactions.

Question 26

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 27

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

Question 28

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 29

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

Question 30

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

Question 31

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

Question 32

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