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Chem 212 Alkyl Halide Problems 4

This document provides 12 problems involving alkyl halide reactions and their mechanisms. It asks the student to show the products and appropriate stereochemistry for reactions involving alkyl halides with nucleophiles like CN-, I-, OH-, and N3-. It also provides 6 pairs of reactions and asks the student to predict which will be faster in each pair and explain why based on leaving group ability and solvent effects.

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1K views1 page

Chem 212 Alkyl Halide Problems 4

This document provides 12 problems involving alkyl halide reactions and their mechanisms. It asks the student to show the products and appropriate stereochemistry for reactions involving alkyl halides with nucleophiles like CN-, I-, OH-, and N3-. It also provides 6 pairs of reactions and asks the student to predict which will be faster in each pair and explain why based on leaving group ability and solvent effects.

Uploaded by

kevinamy
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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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

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