Chem 212 Alkyl Halide Problems 3

Chem 212 Alkyl halide problems 3

Provide the products for the following reactions, show the mechanisms, and all relevant stereochemistry.

NaNH2

1.

HO

+ 6.

NH3

Cl H

7.

OH

Br

Br

acetone

Cl H

OH

Br

NaBr

2.

H2O

NH3 EtOH N H

Br Br

3.

CN

+

KOH

NaCN

8.

DMSO

Cl H

+

AgNO3

4. Cl H

OEt

OEt

OEt +

I

CsI MeOH

Cl H

9.

AgNO3 EtOH

EtOH

5.

Br

Br

10.

NaCN

CN

DMSO

I

11. Predict the effect of the changes given below on the rate of the following reaction: NaCN Cl

CN

MeOH

a) change the halogen from Cl to I.

faster

b) change solvent from MeOH to DMSO

faster

c) change starting material from 1-chloropropane to 2-chloropropaneslower

12. Rank the following sets in order of increasing SN2 reactivity a)

Br

Br

CH3Br fastest

slowest

b) Cl

Cl

I fastest

slowest

c) Cl

Cl

Cl

fastest

slowest

13. Rank the members of the following groups in order of basicity, nucleophilicity, and leaving group ability. Expain your answers. nucleophilicity basicity > CH3CO2 - > H2O

leaving group ability

a) H2O, - OH, CH3CO2 -

-OH

b) Br -, Cl -, F -, I -

F- > Cl- > Br- > I-

I- > Br- > Cl- >F-

I- > Br- > Cl- >F-

- NH > - PH > NH 2 2 3

- PH > - NH > NH 2 2 3

NH3 > -PH2 > -NH2

c) - NH2, NH3, - PH2

-OH

> CH3CO2 - > H2O

H2O > CH3CH2CO2- > -OH

d) H2O, H2S, NH3

NH3 > H2O > H2S

H2S > NH3 > H2O

H2S > H2O > NH3

e) NaF, NaOH, NaSMe

NaOH > NaSMe > NaF

NaSMe > NaOH > NaF

-SMe

> -OH > F-