Chem 212 Provide the products of the following reactions. Be sure to show all appropriate stereochemistry.

Alkyl halide problems 4 Show the mechanism for all the problems.

NaCN 7. KOH
1. Br CN
acetone TsO H

NaN3
8.
NaI I TsO H DMSO N3
2. Br
DMF

H Br

3. Br KOH OH 9. NaOH

NaN3 H Br I
4. Br N3
acetone 10. NaI
H2O

NaCN H Br
5.
acetone NaOMe
TsO H CN 11.
MeOH

6. NaI H Br N3

acetone NaN3
TsO H 12.
I DMF

For the following pairs of reactions predict which will be faster and explain why.

13. a) NaN3 16. a) NaCN

Cl N3 Br CN
EtOH MeOH

b) NaN3 faster b) NaCN faster

I N3 Br CN polar, aprotic solvent
EtOH better leaving group DMF

faster,
14. a) H 2O faster 17. a) NaOH both are in a poor SN2
Br OH
tertiary carbocation solvent, but
heat more stable Br H2O OH hydroxide is better
nucleophile
b) Br H2O OH b) NaO2CCH3 O
heat Br H2O
H H O

15. a) Br SH 18. a) NaCN

NaSH
Br DMF CN
faster faster
b) NaSH primary over b) NaCN primary over
Br SH
secondary Br CN secondary
DMF