Deck 24: Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution and Α-Substitution Reactions

Question 1

Rank the following molecules, A-D, in order of their relative electrophilicity (where 1 is the most electrophilic and 4 is the least electrophilic):

A) Molecule A
B) Molecule B
C) Molecule C
D) Molecule D

Answer 1

B, D, C, A

Question 2

Rank the following molecules, A-D, in order of their relative acidity (where 1 is the most acidic and 4 is the least acidic):

A) Molecule A
B) Molecule B
C) Molecule C
D) Molecule D

Answer 2

B, C, D, A

Question 3

For the following reaction, pick out a suitable rate profile from A-D for this transformation:

A) A
B) B
C) C
D) D

Answer 3

C

Question 4

For the following reaction, pick out the products. Please select all that apply.

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

Question 5

From the following reactions, A-D, pick out those which lead to the formation of ethyl acetate (ethyl ethanoate). Please select all that apply.

A) A
B) B
C) C
D) D

Question 6

For the following transformation, deduce whether it is an oxidation, reduction or neither:

A) Oxidation
B) Reduction
C) Neither

Question 7

Rank the following molecules, A-D, in order of their ability to form enols (with 1 being most able and 4 the least able):

A) Molecule A
B) Molecule B
C) Molecule C
D) Molecule D

Question 8

For the following reaction, pick out the major product:

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

Question 9

For the following reaction, pick out the product:

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

Question 10

For the following reaction, pick out the major product::

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

Question 11

For the following reactions, A-D, pick out those which lead to the formation of 2-methyl-2-phenylethanol. Please select all that apply.

A) A
B) B
C) C
D) D

Question 12

For the following reaction, pick out the major product:

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

Question 13

Which of the following reagents, A-E, are suitable reagents for the following transformation? Please select all that apply.

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

Question 14

Which of the following reagents, A-D, is a suitable reagent for the following transformation?

A) A
B) B
C) C
D) D

Question 15

Which of the following reagents, A-E, is a suitable reagent for the following transformation?

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

Question 16

Which of the following reagents, A-E, is a suitable reagent for the following transformation?

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

Question 17

From the following equilibrium, pick out the approximate equilibrium constant for this process:

A) 10^-0.64
B) 10^-1.56
C) 10^-9
D) 10^-12
E) 10^-16

Question 18

Rank the following molecules, A-D, in order of their relative acidity (where 1 is the most acidic and 4 is the least acidic):

A) Molecule A
B) Molecule B
C) Molecule C
D) Molecule D

Question 19

For the following Claisen reaction, pick out the product:

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

Question 20

For the following reaction, pick out the major product:

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

Question 21

Identify the reaction class for the following reaction:

A) Nucleophilic acyl substitution
B) α-substitution
C) carbonyl-carbonyl condensation
D) nucleophilic alkyl substitution

Question 22

A Dieckmann reaction is an example of what type of process? Please select all that apply.

A) Saponification reaction
B) Claisen condensation reaction
C) An intramolecular reaction
D) S_N2 reaction

Question 23

How can the formation of ethyl butanoate from butanoic acid and ethanol be favoured? Please select all that apply.

A) Add a drying agent (e.g. molecular sieves)
B) Distillation (e.g. using a Dean-Stark trap)
C) Lower reaction temperature (e.g. ice bath)
D) Use water as a solvent
E) Use ethanol as a solvent

Question 24

Predict the major product of the following reaction, at room temperature.

A) A
B) B
C) C
D) D

Question 25

Identify the major enol of methyl 3-oxopentanoate.

A) A
B) B
C) C
D) D