Chem2O6 - 1996/97

Assignment #3 Due: January 8, 1997

1. Predict the principal products of the following reactions, showing stereochemistry where appropriate.

Question 1(a)

Question 1(b)

Question 1(c)

2. The following incomplete reaction sequences give only a starting material and a product that can be prepared from it by a multistep reaction sequence. Show the reagents that would that would be necessary to carry out each transformation, and any major products that would be formed in the intermediate stages.

Question 2(a)

Question 2(b)

Question 2(c)

3. The infrared and 1H nmr spectra of a compound with molecular formula C8H8O2 are shown below. Deduce the structure of the compound from these data.

C8H8O2 - IR Spectrum

C8H8O2 - NMR Spectrum

4. The infrared and 1H nmr spectra of a compound with molecular formula C4H8O3 are shown below. Deduce the structure of the compound from these data.

C4H8O3 - IR Spectrum

C4H8O3 - NMR Spectrum

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

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

Assignments are due at 5pm on Wednesday, January 8 (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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04dec96; wjl