Deck 19: Organic Reaction Mechanisms

Question 1

From the following molecules, pick out the one which is the strongest nucleophile:

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

Answer 1

B

Question 2

Which of the following shows resonance?

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

Answer 2

B

Question 3

Which of the following molecules contain conjugation? Please select all that apply.

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

Answer 3

B, D

Question 4

Which of the following molecules exhibit conjugation? Please select all that apply.

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

Question 5

Which of the following structures do not contribute to the resonance hybrid of a benzyl cation? Please select all that apply.

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

Question 6

From the following carbocations, pick out the most stable:

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

Question 7

Match the following acids to their acidity constant, K_a (in water):

-K_a = 10^-5

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

Question 8

Match the following acids to their acidity constant, K_a (in water):

-K_a = 10^-7

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

Question 9

Match the following acids to their acidity constant, K_a (in water):

-K_a = 10^-16

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

Question 10

Match the following acids to their acidity constant, K_a (in water):

-K_a = 10^-50

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

Question 11

Using the pK_a data provided, pick out the acid that is most dissociated in water.

A) Acid A; pK_a = ?9
B) Acid B; pK_a = 0
C) Acid C; pK_a = +2
D) Acid D; pK_a = +50

Question 12

Which of the following phenols has the largest acidity constant, K_a?

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

Question 13

Toluene can be deprotonated using n-BuLi in THF; pick out its conjugate base:

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

Question 14

From the following molecules, pick out the strongest base:

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

Question 15

From the following molecules, pick out the strongest acid:

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

Question 16

From the following molecules, pick out the strongest base:

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

Question 17

From the following molecules, pick out the weakest base:

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

Question 18

From the following carbocations, pick out the most acidic:

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

Question 19

For the following reaction, deduce whether it involves oxidation, reduction or neither:

A) Oxidation
B) Reduction
C) Neither

Question 20

Pick out the term which describes the following reaction:

A) Radical elimination
B) Nucleophilic substitution
C) Electrophilic addition

Question 21

Pick out the term which describes the following reaction:

A) Chemoselectivity
B) Stereoselectivity
C) Regioselectivity

Question 22

Pick out the terms which describe the following reaction. Please select all that apply.

A) Chemoselectivity
B) Regioselectivity
C) Stereoselectivity

Question 23

Pick out the terms which describe the following reaction. Please select all that apply.

A) Chemoselectivity
B) Regioselectivity
C) Stereoselectivity

Question 24

In general, the more stable the carbanion or carbocation, the higher the equilibrium constant (K) and the greater the concentration of the product carbanion or carbocation at equilibrium.

Question 25

Select those from A-D that are electron donating groups through mesomeric effects (also known as resonance effects).

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

Question 26

Select molecules below that have conjugated double bonds (select all correct answers)

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

Question 27

An electronegative atom (e.g. F) bonded to a carbon chain causes a polarization of the C-C bonds. The notation "- I" is often used to represent this, but to what does this refer?

A) negative inductive effect
B) positive induction effect
C) hyperconjugation
D) resonance

Question 28

The symmetrical cleavage of a covalent bond is called heterolytic cleavage.