Chemistry 331 - Winter 1996
Elements of Organic Chemistry I

Quiz, Chapter 7 - Alkyl Halides

1. (5 points) Starting from methylcyclopropane, write names and structures for all the different monochlorination products that would be expected from free radical chlorination with Cl2 and light. Indicate the ones that would be chiral, and indicate whether they would be expected to be racemic or not.

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2. (5 points) (R)-2-bromobutane is reacted with various nucleophiles of general structure RO-.
Possible mechanisms for reaction include SN1, SN2, E2, and E1.
For each of those four possibilities, indicate:
a) what product you would expect, and
b) how you could tell whether that particular mechanism was followed.

SN1:

The product should be racemic. The rate should depend only on the concentration of RBr and not on RO- .

SN2:

The product should show inversion. The rate should depend on the concentration of both RBr and RO- .

E2:

The rate should depend on the concentration of both RBr and RO- .

E1:

The rate should depend only on the concentration of RBr and not on RO- .