Deck 17: Aldehydes and Ketones: the Carbonyl Group

Question 1

What would be the proper name of the following molecule?

A) 3-formyl-2-butanol
B) 2-(hydroxyethyl)propanal
C) 3-hydroxy-2-methylbutanal
D) 2,3-dimethylpropan-3-ol-1-al
E) 1-methyl-3-formyl-1-propanol

Answer 1

3-hydroxy-2-methylbutanal

Question 2

What would be the major product of the following reaction sequence?

A)

B)

C)

D)

E)

Answer 2

Question 3

What would be the expected product of the following reaction sequence?

A)

B)

C)

D)

E)

Answer 3

Question 4

What would you expect to result from the following reaction?

A)

B)

C)

D)

E)

Question 5

Which of the following could not be involved in a given Wittig reaction?

A)

B)

C)

D)

E) All of these are involved.

Question 6

Which of the following represents an oxaphosphetane intermediate formed during a Wittig reaction?

A)

B)

C)

D)

E)

Question 7

What would be the major product of the following reaction?

A)

B)

C)

D)

E)

Question 8

What product would you expect from the following reaction?

A)

B)

C)

D)

E)

Question 9

Which of the following is a typical ¹³C-NMR shift value for a carbonyl carbon?

A) 208 ppm
B) 29.3 ppm
C) 9.8 ppm
D) 45.2 ppm
E) 1700 cm^-1

Question 10

Indicate which side,if any,would be favored in the reaction shown below.

A) To the right
B) To the left
C) Equally to both sides
D) This reaction cannot occur
E) A different product would be favored.

Question 11

Indicate to which side,if any,the following equilibrium lies:

A) To the right
B) To the left
C) Equally to right and left
D) Reaction cannot occur
E) A different product is formed

Question 12

What is the major organic product of the reaction below?

A)

B)

C)

D)

E)

Question 13

Predict the major organic product of the following reaction sequence.

A)

B)

C)

D)

E)

Question 14

Suppose that a special catalyst was discovered that would allow an equilibrium to occur between the two molecules shown below.To which side,if any,would you expect the equilibrium to lie?

A) To the right
B) To the left
C) Equally to the right and left
D) There is no way to predict this.
E) These molecules are not isomers.

Question 15

What would be the best name of the following compound?

A) 6-oxo-2-hexanone
B) 5-oxohexanal
C) Hexan-5-one-1-al
D) 1,5-dioxohexane
E) 2-oxohexanal

Question 16

What product would you expect from the following reaction? (Hint: In what form does the reactant actually exist?)

A)

B)

C)

D)

E)

Question 17

Which of the following would react with Ag⁺ under basic conditions?

A)

B)

C) CH₃CH₂CO₂CH₂CH₃
D)

E)

Question 18

To which side (if any)would the following equilibrium lie?

A) To left
B) To right
C) Equally to the right and left
D) Reaction cannot occur at all
E) Equilibrium favors a different product.

Question 19

Why is the reaction of the type shown below usually done?

A) To make the  hydrogens more acidic
B) To protect a ketone or aldehyde carbonyl
C) To make the molecule more reactive
D) To make an aldehyde or ketone less water soluble
E) To increase the oxygen content

Question 20

What test is used to detect the presence of an aldehyde?

A) Tollen's
B) Lucas
C) Fehling
D) A and B
E) A and C

Question 21

At which atom of the following structure will a nucleophile attack?

A) At the carbonyl oxygen
B) At the carbonyl carbon
C) At the methyl carbon
D) At the ether oxygen
E) At the aldehyde hydrogen

Question 22

Which of the following structures represents: (Z)-3-fluoro-3-octen-2,5-dione?

A)

B)

C)

D)

E)

Question 23

Predict the product of the following reaction:

A)

B)

C)

D) CH₃OH
E) Both A and C

Question 24

Predict the product from the following reaction sequence.

A)

B)

C)

D)

E)

Question 25

Old bottles of benzaldehyde (a liquid that smells like cherries)are often observed to have crystals on the bottom; what is the identity of this solid?

A)

B)

C)

D)

E)

Question 26

What is the name of the reaction by which aldehydes and ketones are converted directly to alkenes?

A) Friedel-Crafts
B) Williamson
C) Wittig
D) Hofmann
E) Fischer

Question 27

The IUPAC name for piperitone is

A) 6-isopropyl-3-methyl-2-cyclohexenone.
B) 2-isopropyl-5-methyl-5-cyclohexenone.
C) 6-isopropyl-3-methylcyclohexanone.
D) 1-methyl-4-isopropylcyclohexen-3-one.
E) 6-isopropyl-3-methyl-3-cyclohexenone.

Question 28

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 29

What reactants would be required to prepare the oxime shown below?

A)

B)

C)

D)

E) None of these would produce the desired product.

Question 30

Given the geometry of nitrogen (which is not represented properly here),the oxime shown below could exist as how many isomers?

A) Only one isomer is possible.
B) Two enantiomers are possible.
C) Two diastereomers are possible.
D) Three stereoisomers are possible.
E) There are no stereoisomers of this compound possible.

Question 31

Which is the structure of 3,7-dimethyl-2,6-octadienal?

A)

B)

C)

D)

E)

Question 32

Predict the product from the following reaction.

A)

B)

C)

D)

E)