Deck 14: Aldehydes and Ketones: Nucleophilic Addition Reactions

Question 1

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.

Answer 1

Benzaldehyde is the electrophile and HCN is the nucleophile in this reaction.

Question 2

Instructions: Consider the data below to answer the following question(s).
C₇H₁₄O


Refer to instructions.Interpret the ¹H NMR data.

Answer 2

The ¹H NMR indicates that there are only three different kinds of hydrogen in the molecule.The 6 H triplet is due to two equivalent CH₃ groups next to two equivalent CH₂ groups,the 4 H triplet is due to two equivalent CH₂ groups next to two other equivalent CH₂ groups,shifted by a C=O,and the 4 H multiplet is two equivalent CH₂ groups between a CH₂ and a CH₃.

Question 3

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.

Answer 3

dependent on the structure of the carbonyl.

Question 4

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 5

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.

A)A
B)B
C)C
D)D

Question 6

Predict the products of the following reactions.

Question 7

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 8

The substance formed in the following reaction is called:

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

Question 9

Instructions: Consider the data below to answer the following question(s).
C₇H₁₄O


Refer to instructions.What functional group is indicated by the IR data?

Question 10

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

Question 11

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 12

Instructions: Consider the data below to answer the following question(s).
C₇H₁₄O


Refer to instructions.Calculate the degree of unsaturation for this compound.

Question 13

Instructions: Consider the data below to answer the following question(s).
C₇H₁₄O

Refer to instructions.Interpret the mass spectral data.

Question 14

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

Predict:

Question 15

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 16

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

Question 17

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 18

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 19

Instructions: Consider the data below to answer the following question(s).
C₇H₁₄O


Refer to instructions.Propose a structure consistent with the spectral data presented above.

Question 20

Predict the products of the following reactions.

Question 21

What is the IUPAC name of the following compound?

A)(2S,4R)-dimethylpentanal
B)(2S,4S)-dimethylpentanal
C)(R)-2,4-dimethylpentanal
D)(S)-2,4-dimethylpentanal

Question 22

Based on the following IR spectrum,
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-06-08)
The compound represented would be classified as an:

A)aromatic ketone
B)aromatic aldehyde
C)aliphatic ketone
D)aliphatic aldehyde

Question 23

Draw the product(s)of the following reaction.

Question 24

What is the name of the major organic product obtained from the following reaction?

A)2,3-dimethylheptan-3-ol
B)2,4-dimethylheptan-4-ol
C)3,5-dimethylheptan-4-ol
D)3,5-dimethylheptan-3-ol

Question 25

Predict whether the following reactions of the depicted carbonyl containing compounds and amines will result in the formation of an enamine or an imine.

Question 26

Which of the following would correctly describe the respective ¹³C NMR and ¹H NMR spectra for the indicated atoms for the compound shown below?

A)Atom 1 would produce a peak at 205 and atom 2 would appear as a singlet.
B)Atom 1 would produce a peak at 195 and atom 2 would appear as a singlet.
C)Atom 1 would produce a peak at 205 and atom 2 would appear as a triplet.
D)Atom 1 would produce a peak at 195 and atom 2 would appear as a triplet.

Question 27

What is the correct assignment of the functional groups in each of the following compounds?

A)1 = amine;2 = imine;3 = enamine
B)1 = enamine;2 = imine;3 = amine
C)1 = imine;2 = enamine;3 = amine
D)1 = amine;2 =enamine;3 = imine

Question 28

Draw the structure of the product obtained from the following reaction.

Question 29

In the box,what is the name of the reactant used in the following reaction?

A)2-methylhept-4-ene
B)heptan-4-one
C)2-methylheptan-4-one
D)2-methylhep-3-ene-4-one

Question 30

Synthesize the following alkene through the Wittig reaction of a carbonyl compound and a phosphorus ylide.