Exam IV

Question 1

H2O

Answer 1

Weak Nucleophile, Weak Base, pka of conj acid = 0, good leaving group

Question 2

ROH

Answer 2

Weak Nu, Weak B, good leaving group

Question 3

H3N

Answer 3

Weak Nu, Weak B, pka of conj. acid = 9.4

Question 4

R2NH

Answer 4

Weak Nu, Weak B

Question 5

I-

Answer 5

Strong Nu, Weak B, pka of conj. acid = -10, good leaving group

Question 6

Br-

Answer 6

Strong Nu, Weak B, pka of conj. acid = -9, good leaving group

Question 7

Cl-

Answer 7

Strong Nu, Weak B, pka of conj acid = -7, moderate leaving group

Question 8

HS-

Answer 8

Strong Nu, Weak B

Question 9

RS-

Answer 9

Strong Nu, Weak B

Question 10

RCO2-

Answer 10

Strong Nu, Weak B

Question 11

HO-

Answer 11

Strong Nu, Strong B, poor leaving group

Question 12

RO-

Answer 12

Strong Nu, Strong B, pka of conj. acid > 14, poor leaving group

Question 13

H2N-

Answer 13

Strong Nu, Strong B, pka of conj. acid = 36, poor leaving group

Question 14

R2N-

Answer 14

Strong Nu, Strong B

Question 15

H3C-

Answer 15

Strong Nu, Strong B

Question 16

R-

Answer 16

Strong Nu, Strong B

Question 17

NHR-

Answer 17

Strong Nu, Strong B

Question 18

CN-

Answer 18

Strong Nu, Weak B

Question 19

CH3COO-

Answer 19

Strong Nu, Weak B, pka of conj. acid = 4.75, moderate leaving group

Question 20

N3-

Answer 20

Strong Nu, Weak B

Question 21

R3N

Answer 21

Weak Nu, Weak B

Question 22

RSH

Answer 22

Weak Nu, Weak B

Question 23

TsO-

Answer 23

pka of conj. acid = -2.8, good leaving group

Question 24

TfO-

Answer 24

pka of conj. acid = -13, good leaving group

Question 25

More stable nucleophile

Answer 25

Slower SN2 Reaction

Question 26

(-) Charge

Answer 26

Stronger Nucleophile

Question 27

Secondary & Tertiary

Answer 27

SN1/E1

Question 28

Primary, Secondary, & Tertiary

Answer 28

E2

Question 29

Secondary, Primary, Methyl

Answer 29

SN2

Question 30

H-bond

Answer 30

Polar Protic

Question 31

No H-bond

Answer 31

Polar Aprotic