Sn1 vs Sn2

Question 1

Concerted

Answer 1

Sn2

Question 2

1 step

Answer 2

Sn2

Question 3

2 steps

Answer 3

Sn1

Question 4

Bimolecular

Answer 4

Sn2

Question 5

Unimolecular

Answer 5

Sn1

Question 6

Always inverts the substrate’s original stereochemistry

Answer 6

Sn2

Question 7

Creates a racemic mixture of products; half retains original stereochemistry, half inverts it

Answer 7

Sn1

Question 8

Nucleophile attacks in only one direction

Answer 8

Sn2

Question 9

Nucleophile attacks from either above or below

Answer 9

Sn1

Question 10

LG leaving is the rate determining step

Answer 10

Sn1

Question 11

Kinetics/rate of rxn is dependent only on the substrate (LG)

Answer 11

Sn1

Question 12

Kinetics/rate of rxn is dependent on both the substrate (LG) and on the nucleophile

Answer 12

Sn2

Question 13

Uses two curved arrows in a single concerted step

Answer 13

Sn2

Question 14

Uses two curved arrows, one in each step

Answer 14

Sn1

Question 15

Proceeds via a carbocation intermediate

Answer 15

Sn1

Question 16

Unreactive to tertiary substrates

Answer 16

Sn2

Question 17

Most reactive to primary and secondary substrates

Answer 17

Sn2

Question 18

Most reactive to tertiary substrates

Answer 18

Sn1

Question 19

Least reactive to secondary and primary substrates

Answer 19

Sn1

Question 20

Strong nucleophile

Answer 20

Sn2

Question 21

Weak nucleophile

Answer 21

Sn1

Disfavors Sn2, allows Sn1 to successfully compete

Question 22

Polar aprotic solvent

Answer 22

Sn2

Question 23

Needs the least steric hindrance

Answer 23

Sn2

Question 24

Needs the most stable carbocation possible

Answer 24

Sn1