Chemistry 331 - Winter 1996
Elements of Organic Chemistry I

Homework, Chapter 7 - Alkyl Halides

McMurry, pp 228 - 231:

Problems 7.24, 26-32, 34-39, 42, 48-52, 54, 55

See the Study Guide for answers for the problems from the text.

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1. Consider the three constitutional isomers:

1-bromo-3-methylbutane
2-bromo-3-methylbutane
2-bromo-2-methylbutane

a) Select the isomer that will be most reactive in an SN2 reaction and illustrate its SN2 and E2 mechanisms when it reacts with sodium methoxide (NaOCH3).

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b) Select the isomer that will be most reactive in an SN1 reaction and illustrate its SN1 and E1 mechanisms when it reacts with methanol (CH3OH).

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c) Select an isomer that could be prepared in optically active form and show the stereochemistry of the SN2 reaction of the (R) enantiomer with azide anion (N3-).

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2. Write out all of the possible isomers that could be formed from radical chlorination (monochloro products) of (S)-3-methylheptane. Identify the expected stereochemistry of each product.