Deck 14: Aldehydes and Ketones: Nucleophilic Addition Reactions

Question 1

Draw structures corresponding to each of the following names.
Draw:
cyclohexen-2-one

Answer 1

Question 2

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

Answer 2

an acetal

Question 3

Consider the data below to answer the following question(s).
C₇H₁₄O
IR:
1715 cm−¹
MS:
M⁺ at m/z = 114, α-cleavage fragment at m/z = 71.
McLafferty rearrangement fragment at m/z = 86.
¹H NMR:
0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet)
Refer to instructions. Interpret the mass spectral data.

Answer 3

A fragment at m/z = 71 indicates a loss of 43, or a C₃H₇ group, from α-cleavage. A fragment at m/z = 86 indicates a loss of 28, or an ethylene group, from McLafferty rearrangement (transfer of a hydrogen atom from the gamma carbon to the carbonyl oxygen with concommitant breaking of the bond between the alpha and beta carbon).

Question 4

Consider the data below to answer the following question(s).
Cyanohydrins are important intermediates in the synthesis of α-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 5

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

Question 6

α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β 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 7

α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β 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 8

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

Question 9

Consider the data below to answer the following question(s).
C₇H₁₄O
IR:
1715 cm−¹
MS:
M⁺ at m/z = 114, α-cleavage fragment at m/z = 71.
McLafferty rearrangement fragment at m/z = 86.
¹H NMR:
0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet)
Refer to instructions. Interpret the ¹H NMR data.

Question 10

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

Question 11

Consider the data below to answer the following question(s).
C₇H₁₄O
IR:
1715 cm−¹
MS:
M⁺ at m/z = 114, α-cleavage fragment at m/z = 71.
McLafferty rearrangement fragment at m/z = 86.
¹H NMR:
0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet)
Refer to instructions. Calculate the degree of unsaturation for this compound.

Question 12

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 13

Consider the data below to answer the following question(s).
C₇H₁₄O
IR:
1715 cm−¹
MS:
M⁺ at m/z = 114, α-cleavage fragment at m/z = 71.
McLafferty rearrangement fragment at m/z = 86.
¹H NMR:
0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet)
Refer to instructions. What functional group is indicated by the IR data?

Question 14

Consider the data below to answer the following question(s).
Cyanohydrins are important intermediates in the synthesis of α-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 15

Consider the reaction below to answer the following question.
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

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 17

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

Question 18

Provide IUPAC names for each structure below.
Name:

Question 19

Consider the reaction below to answer the following question.
The substance formed in the following reaction is called:

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

Question 20

Provide IUPAC names for each structure below.
Name:

Question 21

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 22

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 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 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 25

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 26

Draw the product(s) of the following reaction.

Question 27

Predict the products of the following reactions.

Question 28

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 29

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

Question 30

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 31

Consider the data below to answer the following question(s).
C₇H₁₄O
IR:
1715 cm−¹
MS:
M⁺ at m/z = 114, α-cleavage fragment at m/z = 71.
McLafferty rearrangement fragment at m/z = 86.
¹H NMR:
0.92 δ (6 H, triplet), 1.59 δ (4 H, multiplet), 2.36 δ (4 H, triplet)
Refer to instructions. Propose a structure consistent with the spectral data presented above.

Question 32

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

Question 33

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

Question 34

Predict the products of the following reactions.

Question 35

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

Question 36

Based on the following IR spectrum,

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