Deck 19: Aldehydes and Ketones: Nucleophilic Addition Reactions

Question 1

Exhibit 19-1
Consider the reaction below to answer the following question(s):
Refer to Exhibit 19-1.The substance formed on addition of water to an aldehyde or ketone is called a hydrate or a/an:

A)vicinal diol
B)geminal diol
C)acetal
D)ketal

Answer 1

geminal diol

Question 2

Draw: trans-3-isopropylcyclohexanecarbaldehyde

Answer 2

Question 3

Draw: 2-cyclohexenone

Answer 3

Question 4

Name:

Question 5

Exhibit 19-1
Consider the reaction below to answer the following question(s):
Refer to Exhibit 19-1.Write the complete stepwise mechanism for the reaction shown above.Show all intermediate structures and all electron flow with arrows.

Question 6

Exhibit 19-1
Consider the reaction below to answer the following question(s):
Refer to Exhibit 19-1.The exact position of the equilibrium between ketones/aldehydes and their hydrates depends on the structure of the carbonyl compound.Although the equilibrium favors the carbonyl compound in most cases,cyclopropanone forms a stable hydrate.Explain this phenomenon based on the structures of cyclopropanone and its hydrate.

Question 7

Draw: 5,5-dimethyl-1,3-cyclohexanedione (dimedone)

Question 8

Name:

Question 9

Draw: 2,2,2-trichloroethanal (chloral)

Question 10

Name:
​

Question 11

What is the correct structure for 2-hydroxyacetophenone?

A)
B)
C)
D)

Question 12

Exhibit 19-2
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.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
Refer to Exhibit 19-2.The reaction of benzaldehyde with hydrogen cyanide is catalyzed by the addition of a small amount of KCN.Write the complete reaction mechanism for the KCN-catalyzed reaction.Show all electron flow with arrows and show all intermediate structures.

Question 13

Name:

Question 14

Exhibit 19-2
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.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
Refer to Exhibit 19-2.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 15

Draw: benzophenone

Question 16

Exhibit 19-2
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.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
Refer to Exhibit 19-2.Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.

Question 17

Enamines formed from the cyclic secondary amine pyrrolidine are important intermediates in the synthesis of 1,5-diketones. On the structures provided below,draw arrows showing electron flow for the reaction mechanism for the acetic acid-catalyzed formation of an enamine from cyclohexanone and pyrrolidine.

Question 18

Name:

Question 19

Exhibit 19-1
Consider the reaction below to answer the following question(s):
Refer to Exhibit 19-1.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 20

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Question 21

In the Wittig reaction,a phosphorus ylide adds to a ketone or aldehyde to yield an alkene.Write the complete stepwise mechanism for the Wittig reaction shown below.Show all intermediate structures and all electron flow with arrows.

Question 22

Exhibit 19-9
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 (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet)
Refer to Exhibit 19-9.What functional group is indicated by the IR data?

Question 23

Exhibit 19-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 19-3.The nucleophile in this reaction is:

Question 24

Consider the following structure.Atoms other than carbon and hydrogen are labeled. Oxidation of this compound yields:

A)
B)
C)
D)No reaction

Question 25

Exhibit 19-4
α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon,as shown below.
Refer to Exhibit 19-4.Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.

Question 26

Name the following compound.Atoms other than carbon and hydrogen are labeled.

Question 27

Exhibit 19-9
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 (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet)
Refer to Exhibit 19-9.Interpret the ¹H NMR data.

Question 28

Exhibit 19-9
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 (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet)
Refer to Exhibit 19-9.Interpret the mass spectral data.

Question 29

Exhibit 19-10
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,
no McLafferty rearrangement fragment
¹H NMR: Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS
Refer to Exhibit 19-10.Propose a structure for this compound.

Question 30

Based only on the spectrum below,what is inferred about the compound used to produce the spectrum?

A)aromatic
B)aldehyde
C)para disubstituted
D)ethyl substituent
E)All of the above are evident from the spectrum.

Question 31

Exhibit 19-2
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.Unfortunately,when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
Refer to Exhibit 19-2.Formulate a reasonable mechanism for the reaction of the cyanohydrin of benzaldeyhe,shown above,with aqueous NaOH.Show all intermediate structures and all electron flow with arrows.

Question 32

Exhibit 19-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 19-3.The catalyst in this reaction is:

Question 33

Exhibit 19-10
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,
no McLafferty rearrangement fragment
¹H NMR: Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS
Refer to Exhibit 19-10.Interpret the ¹H NMR spectrum.

Question 34

Exhibit 19-4
α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon,as shown below.
Refer to Exhibit 19-4.This reaction is called _____ reaction.

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

Question 35

Exhibit 19-9
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 (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet)
Refer to Exhibit 19-9.Propose a structure consistent with the spectral data presented above.

Question 36

Exhibit 19-10
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,
no McLafferty rearrangement fragment
¹H NMR: Spectrum obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS
Refer to Exhibit 19-10.Interpret the mass spectral data for this compound.

Question 37

Exhibit 19-9
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 (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet)
Refer to Exhibit 19-9.Calculate the degree of unsaturation for this compound.

Question 38

Exhibit 19-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 19-3.Write the complete stepwise mechanism for this reaction.Show all electron flow with arrows and show all intermediate structures.

Question 39

Exhibit 19-3
Consider the reaction below to answer the following question(s).
Refer to Exhibit 19-3.The product of this reaction is called:

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

Question 40

Which of the labeled peaks would allow the distinction of an aldehyde from a ketone based on this spectrum?

A)1
B)2
C)3
D)4

Question 41

Draw the mechanism of the Grignard reaction involving acetone and methyl magnesium chloride.​

Question 42

If the following substance were treated with HCN followed by aqueous acid and heat, which of the following would be produced? Atoms other than carbon and hydrogen are labeled.

A)
B)
C)
D)both b and c
E)all of the above

Question 43

Of the types of reactions that characterize carbonyl groups,how is the following reaction classified?

A)nucleophilic addition
B)nucleophilic acyl substitution
C)α substitution
D)carbonyl condensation

Question 44

Which of the following reagents could be used to convert 3-cyclopentyl-2-methylpropanal to the following substance? Atoms other than carbon and hydrogen are labeled.

A)CrO₃
B)O₃
C)DIBAH
D)LiAlH₄

Question 45

​Draw the mechanism of the nucleophilic addition reaction of pentanal to give an alcohol.

Question 46

The following substance is heated in the presence of aqueous NaOH.Atoms other than carbon and hydrogen are labeled. The product of the reaction is:

A)
B)
C)
D)both b and c
E)all of the above

Question 47

​Draw the mechanism of the nucleophilic addition reaction involving acetaldehyde and a neutral nucleophile,in acidic conditions.

Question 48

Which of the following functional groups does not contain a carbonyl group?

A)ester
B)carboxylic acid
C)ketone
D)phenol