Substituiton And Elimination Rxns

Question 1

Strong Base + Weak Nucleophile + 1°

Answer 1

E2

Question 2

Strong Base + Weak Nucleophile + 2 °

Answer 2

E2

Question 3

Strong Base + Weak Nucleophile + 3 °

Answer 3

E2

Question 4

Strong Base + Strong Nucleophile + 1 °

Answer 4

E2 = Minor Product
SN2 = Major Product

Question 5

Strong Base + Strong Nucleophile + 2 °

Answer 5

E2 = Major product
SN2 = Minor Product

Question 6

Strong Base + Strong Nucleophile + 3 °

Answer 6

E2

Question 7

Weak Base + Strong Nucleophile + 1 °

Answer 7

SN2

Question 8

Weak Base + Strong Nucleophile + 2°

Answer 8

SN2

Question 9

Weak Base + Strong Nucleophile + 3 °

Answer 9

SN1

Question 10

Weak Base + Weak Nucleophile + 1 ° or 2 °

Answer 10

Typically too unstable to form

Question 11

Weak Base + Weak Nucleophile + 3 °

Answer 11

SN1 and E1 (equally)

Question 12

3 ° + weak Nucleophile/ weak base

Answer 12

SN1/E1

Question 13

2 ° + weak Nucleophile/weak base

Answer 13

SN1/E1, just not efficient or very stable

Question 14

3 ° + strong Nucleophile/ weak base

Answer 14

SN1

Question 15

2 ° + strong Nucleophile/ weak base

Answer 15

SN2

Question 16

1 ° + strong Nucleophile/ weak base

Answer 16

SN2

Question 17

CH3 (methyl) + strong Nucleophile

Answer 17

SN2

Question 18

3 ° + strong base

Answer 18

E2

Question 19

Reminder: Does SN2 occur at 3 °?

Answer 19

No, 3 ° for SN2 is unstable
(CH3 > 1 ° > 2 °)

Question 20

2 ° + strong Nucleophile/ strong base

Answer 20

E2 = major
SN2 = minor

Question 21

1 ° + strong Nucleophile/ strong base

Answer 21

SN2 = major
E2= minor

Question 22

2 ° + strong, bulky base

Answer 22

E2

Question 23

1 ° + strong, bulky base

Answer 23

E2

Question 24

Reminder: what rxns do not occur at 1°?

Answer 24

SN1 and E1

Question 25

Weak Nucleophiles, Weak Bases

Answer 25

H20 (water)
ROH (alcohol)
RCOOH (carboxylic acid)

Question 26

Strong Nucleophiles, Weak Bases

Answer 26

CN-, N3-, Cl-, Br-, I-, RS-, HS- (hydro sulfide), RSH (thiol), H2S, RNH2 (amine), R3P

Question 27

Strong Nucleophile, Strong Base

Answer 27

OH-, RO- (alkoxide)

Question 28

Strong, bulky base

Answer 28

t-buO- (tert butoxide), Et3N (trierhylamine), DBN, DBU…

Question 29

SN2 Substrate Stability…

Answer 29

CH3 > 1 ° > 2 °

Question 30

E2 Substrate Stability…

Answer 30

3 ° > 2 ° > 1 °

Question 31

SN1 substrate stability

Answer 31

3 ° > 2 °

Question 32

E1 substrate stability

Answer 32

3 ° > 2 °