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Testing Your Organic Chemistry Knowledge to Reinforce ...

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<strong>Testing</strong> <strong>Your</strong> <strong>Organic</strong> <strong>Chemistry</strong> <strong>Knowledge</strong> <strong>to</strong> <strong>Reinforce</strong> Comprehension and<br />

Understanding using Web-based Multiple Choice Questions<br />

Andrew Boa and Jason Eames*<br />

Department of <strong>Chemistry</strong>, University of Hull<br />

a.n.boa@hull.ac.uk; j.eames@hull.ac.uk<br />

519. Product 10<br />

For the following reaction, pick out the product Z:<br />

a. A<br />

b. B<br />

c. C<br />

d. D<br />

*e. E<br />

Correct Answer Reply:<br />

The reducing agent lithium aluminium deuteride delivers two deuteride ions (D - ) <strong>to</strong> the<br />

electrophilic carbonyl carbon. The reaction proceeds via the intermediate aldehyde C, but<br />

on final addition of water (in step 2 of the mechanism), pro<strong>to</strong>nation of the alkoxide<br />

intermediate gives the alcohol E.

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