Deck 13: Aldehydes and Ketones-Nucleophilic Addition

Question 1

What is the product of the following reaction?

A) III
B) I
C) II
D) IV

Answer 1

I

Question 2

What is the product of the following reaction?

A) IV
B) I
C) II
D) III

Answer 2

I

Question 3

How would the following compounds be distinguishable using IR and ¹H NMR spectroscopy?

A) The¹H NMR spectrum of compound I will have two singlets.
B) The¹H NMR spectrum of compound II will have one triplet at a chemical shift of about 4.
C) The¹H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.
D) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.

Answer 3

The¹H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.

Question 4

What is the product?

A) II
B) I
C) III
D) IV

Question 5

What is the IUPAC name for the following compound?

A) Tert-butyl aldehyde
B) 2,2-Dimethylpropanal
C) Pivaldehyde
D) 2,2-Dimethylpentanal

Question 6

What is the product of the following reaction?

A) IV
B) I
C) II
D) III

Question 7

What needs to be done to make the following reaction proceed?

A) Add an acid catalyst only.
B) Heat the reaction and add an acid catalyst.
C) Heat the reaction.
D) Add a base catalyst only.

Question 8

Name the following aldehyde.

A) 1-Methylcyclopentanylcarbaldehyde
B) 2-Methylcyclopentanecarbaldehyde
C) 1-Methylcyclopentanal
D) 2-Methylcyclopentanal

Question 9

What is the major product of the following reaction?

A) III
B) II
C) IV
D) I

Question 10

What is the driving force for the Wittig reaction?

A) The elimination of triphenylphosphine oxide
B) The formation of an alkene
C) The formation of a phosphonium salt
D) The deprotonation of a phosphonium salt

Question 11

What is the product of the following reaction?

A) III
B) II
C) IV
D) I

Question 12

What is the major product of the following reaction?

A) III
B) II
C) IV
D) I

Question 13

Using¹H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?

A) A ketone has a signal around 200 ppm.
B) An aldehyde has a C-H stretch (one or two) between 2700-2830 cm^-1.
C) A ketone has signals around 2-3 ppm.
D) An aldehyde has a proton signal between 9-10 ppm.

Question 14

What is the product of the following reaction?

A) IV
B) II
C) I
D) III

Question 15

What is the product of the following reaction?

A) II
B) IV
C) I
D) III

Question 16

Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C. What accounts for this difference in boiling points?

A) Butanal is less sterically hindered than butanol.
B) Butanol is polar while butanal is not polar.
C) Butanol can exhibit dipole-dipole interactions while butanal cannot.
D) Butanol can hydrogen bond and butanal cannot hydrogen bond.

Question 17

What is the product of the following reaction?

A) I
B) III
C) IV
D) II

Question 18

What is the product of the following reaction?

A) IV
B) II
C) I
D) III