Predicting Product (Ch.7)

Question 1

Strong base, weak nucleophile (1, 2, 3 prime)

Answer 1

E2

Question 2

Strong base, strong nucleophile (1,2, 3 prime)

Answer 2

1) SN2 and E2 (favors SN2)
2) E2 and SN2 (favors E2)
3) E2

Question 3

Weak base, strong nucleophile

Answer 3

1) SN2
2) SN2
3) SN1

Question 4

Weak base, weak nucleophile

Answer 4

1) X
2) X
3) SN1 and E1 (equal change)

Question 5

Steps of SN2 reaction

Answer 5

• backside nucleophilic attack

Question 6

Steps of E2 reaction

Answer 6

• loss of leaving group and proton transfer

Question 7

Steps of SN1 reaction

Answer 7

1. loss of leaving group
2. nucleophilic attack
3. proton transfer

Question 8

Steps of E1 reaction

Answer 8

1. loss of leaving group
2. proton transfer

Question 9

Type of SN2 reagent and examples?

Answer 9

Strong nucleophiles: - I-, Br-, Cl-, HS-, OH- RS-, RO-, NC-

Question 10

Type of E2 reagent and examples?

Answer 10

Strong Base: OH-, -OEt, t-BuO-, NaH, DBN, DBU

Question 11

Type of SN1 reagent and examples?

Answer 11

Solvent: EtOH, H2O, MeOH, or strong nucleophile

Question 12

Type of E1 reagent and examples?

Answer 12

weak base/nucleophile: H2O, MeOH, EtOH

Question 13

Product of SN2?

Answer 13

if alpha carbon is chiral center, the stereochemistry is inverted

Question 14

Product of E2?

Answer 14

• Zaitsev products: -OH, -OEt
• Hofmann product: t-BuO-

Question 15

Product of SN1

Answer 15

product is a racemic mixture of stereoisomers

Question 16

Product of E1

Answer 16

favors zaitsev