Deck 20: Carboxylic Acid Derivatives

Question 1

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

A)

B)

C)

D)

E)

Answer 1

Question 2

What would account for the fact that the molecule below racemizes easily,despite having three chiral centers?

A) Lactones are configurationally unstable
B) Molecule loses CO₂ easily
C) Enolization occurs easily
D) Intramolecular transesterification occurs easily
E) This molecule is not chiral.

Answer 2

Intramolecular transesterification occurs easily

Question 3

What would be the organic product of the following reaction?

A)

B)

C)

D)

E) None of these.

Answer 3

Question 4

Rank the following carboxylic acid derivatives in order of decreasing reactivity toward hydrolysis (most reactive on left):

A) D > B > A > C
B) C > A > B > D
C) B > D > A > C
D) A > B > D > C
E) D > B > C > A

Question 5

What would be the major expected product from the reaction shown below?

A)

B)

C)

D)

E)

Question 6

Which of the reactions listed below would produce benzyl acetate (= benzyl ethanoate)?

A)

B)

C)

D) two of these
E) all of these

Question 7

What type of functional group do the natural products known as waxes have?

A) Ester
B) Amide
C) Carboxylic acid
D) Alcohol
E) Amine

Question 8

What would be the organic product of the following reaction?

A)

B)

C) mixture of A and B
D) None of these.
E) No reaction occurs.

Question 9

What would be the name of the following cyclic ester?

A) ( $\gamma$ -valerolactone)
B) ( $\beta$ -butyrolactone)
C) 2-methyl- $\gamma$ -butyrolactone
D) 2-methyl- $\beta$ -butyrolactone
E) 2-methyl- $\gamma$ -valerolactone

Question 10

Which of the following is not an intermediate in the Hofmann rearrangement of ethanamide to methylamine?

A)

B)

C)

D)

E)

Question 11

Lactones are:

A) Cyclic amides
B) Cyclic anhydrides
C) Cyclic esters
D) Cyclic acids
E) Cyclic ketones

Question 12

Which reagent(s)would accomplish the following transformation?

A) CH₃Li
B) CH₃I,NaOH
C) CH₃MgBr
D) (CH₃)₂CuLi
E) either A or C

Question 13

In the reaction shown below,which product(s)would be formed?

A)

B)

C)

D)

E) both A and B

Question 14

How many different CH₃ signals would you expect in the room-temperature proton NMR spectrum of the molecule below?

A) One
B) Two
C) Three
D) Four
E) Five

Question 15

What would be the proper name of the following?

A) 3-nitro-methylbenzoate
B) methyl 3-nitrobenzoate
C) 3-nitro-methoxybenzoate
D) 5-nitro-methylbenzoate
E) 3-nitrocarboxymethylbenzene

Question 16

What would be the product of the following reaction?

A) C₆H₅CO₂H
B) C₆H₅CH₂CO₂H
C) C₆H₅CH₂OH
D) C₆H₅CH₂CH₂NH₂
E) C₆H₅CH₃

Question 17

Which of the following would be properly named as 2-chloroethyl benzoate?

A)

B)

C)

D)

E)

Question 18

What would be the major organic product expected from the following reaction?

A)

B)

C)

D)

E)

Question 19

The product of the following reaction would be:

A)

B)

C)

D)

E)

Question 20

What would be the organic product of the following reaction? (¹⁸O is a rare oxygen isotope.)

A)

B)

C)

D) More than one of these.
E) None of these.

Question 21

What reagent(s)would be required to achieve the following conversion?

A)

B)

C)

D)

E) both A and C

Question 22

How can the importance of the following resonance be evaluated?

A) Charged resonance structures are always more important.
B) The C=O IR stretch for amides is significantly different than for other C=O groups.
C) The water solubility of amides implicates charged structures.
D) The C-N rotational barrier can be determined by NMR.
E) More than one of the above are correct.

Question 23

Predict the product of the following reaction:

A)

B)

C)

D)

E) None of these.

Question 24

Predict the product of the following reaction:

A)

B)

C)

D)

E) no reaction occurs

Question 25

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 26

Which of the following would be most likely to result from saponification of a natural triglyceride?

A)

B)

C)

D)

E)

Question 27

Reduction of which of the following esters with lithium aluminum hydride would yield two molecules of the same alcohol?

A)

B)

C)

D)

E) None of these.

Question 28

A multistep preparation of propylpropanoate from only 1-propanol would require the use of how many of the reagents below (i.e.,what reagents would you need to use if you only had 1-propanol to start with)?

A) Two of the above.
B) Three of the above.
C) Four of the above.
D) All of the above.
E) The preparation cannot be done with only these reagents.

Question 29

When compound X is heated with aqueous acid,acetic acid and acetaldehyde (ethanal)are formed.The proton NMR spectrum of X is shown below.What is the structure of X?

A) CH₂=CHO₂CCH₃
B) CH₂=CHOCH₂CH₃
C) CH₂=C(CH₃)O₂CH
D) CH₃CH=CHO₂CH
E) CH₂=CHCH₂CO₂H

Question 30

What is the product of combining pentanoic acid with thionyl chloride,followed by propanol and base?

A) pentanol
B) pentyl propanoate
C) propyl pentanoate
D) 1-tosyl pentanol
E) 1-chloropentanol

Question 31

What would be the other product of the following reaction?

A)

B)

C)

D)

E)

Question 32

Which of the following reactions will produce N-methyl benzamide?

A)

B)

C)

D) both A and C
E) All of the above.

Question 33

Which of the following is a lactam?

A)

B)

C)

D)

E) Two of these can be considered lactams.

Question 34

Substitutions at sp² carbons do not occur by an S_N2 mechanism,but rather by way of a "tetrahedral intermediate." The tetrahedral intermediate shown could occur in which reaction?

A) methyl propanoate + ammonia
B) propanamide + hydroxide
C) propanoic acid + methanol
D) propanamide + ethanol
E) None of these.

Question 35

What is the relative reactivity of carboxylic acid derivatives toward hydrolysis (left = least reactive)?

A) ester < amide < acid chloride < anhydride
B) amide < ester < acid chloride < anhydride
C) ester < amide < anhydride < acid chloride
D) amide < ester < anhydride < acid chloride
E) The relative reactivities really cannot be compared.

Question 36

What structure is not an intermediate in the following reaction?

A)

B)

C)

D)

E) None of the above.

Question 37

Place the following compounds in order of increasing rate of hydrolysis.

A) I,III,IV,II
B) IV,II,III,I
C) III,I,II,IV
D) I,II,IV,III
E) All carboxylic derivatives exhibit similar reactivities with H₂O.

Question 38

Which of the following reactions will not give a carboxylic acid as a product?

A)

B)

C)

D)

E)

Question 39

What would be the products of the following reaction?

A) CH₃CH₂CH₂CH₂NH(CH₃)+ H₂O
B) CH₃NHC(=O)CH₂CH₂CH₃ + CH₃OH
C) CH₃CH₂CH₂CONH₂ + CH₃CH₂OH
D) CH₃OH + CH₃CH₂CH₂OC(=O)NHCH₃
E) CH₃CH₂CH₂NH(CH₃)COCH₃ + H₂O

Question 40

What would be the product of the following reaction?

A)

B)

C)

D)

E) None of these.

Question 41

Which,if any,functional group in the molecule below would undergo basic hydrolysis most easily?

A) A
B) B
C) C
D) D
E) None of these groups would react.

Question 42

What reagent is needed to complete the reaction shown?

A) ((CH₃)₂CH)₂CuLi
B) KCN/NaOH
C) HOCH(CH₃)₂
D) BrMgCH(CH₃)₂
E) (CH₃)₂CHLi

Question 43

Which functional group has the lowest IR absorption frequency?

A)

B)

C)

D)

E)

Question 44

What is the product from the following reaction?

A)

B)

C)

D)

E)