Chem2O6 - 1996/97

Assignment #4 AnswersDue: February 21, 1997

1.Assign structures to the intermediary compounds shown in the following reaction scheme.

Answer:

2.Start with organic compounds containing no more than three carbons, and using any needed inorganic reagents, outline a synthesis for each of the following.

a) CH3CH(OH)CH2CH2CH3

b)

c)(CH3CH2CH2)2CHOH

d)

Answers:

a)

b)

c)

d)

3. 2-Propenal (sometimes known as acrolein) reacts with HCl to give 3-chloropropanal. Write a mechanism for this reaction. Why is 2-chloropropanal, the formal Markovnikov product, not produced?

Answers:

The key to this problem is realize that acid catalysed additions to a double bond involve the formation of the most stable carbenium ion. The most stable carbenium which can be formed from acrolein is when the proton adds to the oxygen atom.

4. Suggest a mechanism for the reaction shown below. (Note you need not draw out the whole molecule each time but just show the key component of the carbohydrate.)

Answers:

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07 feb 97; rfc/jp