Chem2O6 - 1997/98

Assignment #2 Due: November 14, 1997

1. The sugar glucose has the structure shown below. The squiggly bond to the OH group attached to C1 means that the OH can either be up or down; i.e., there are two structures for glucose. Draw three-dimensional representations of the two molecules in their more stable chair conformations. Assign the stereochemistry at C1 and C5 according to the Cahn-Ingold-Prelog convention.

2. Predict the major products of the following reactions, showing stereochemistry where appropriate. Write mechanisms for each reaction.

3. Each of the following molecules contains two halogens at different positions in the molecule. For each one, explain which of the two halogens will be more reactive in the SN1 reaction.

4. Show how each of the following compounds can be prepared from an alkyl halide.

5. Menthyl chloride reacts with sodium ethoxide in ethanol to give a single product as shown below. Explain why this is the only alkene produced.

Make sure that your answers are STAPLED TOGETHER and labelled with:

Your NAME & STUDENT NO.
Your LAB-SECTION/GROUP/TA (Repeaters should indicate their Tutorial Section)

Assignments are due at 5pm on Friday, November 14 (in your Tutorial Leader's DropBox in ABB). Late assignments will receive a grade of ZERO, unless a medical slip is filed with the Dean's Office.

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30oct97; wjl