organic-synthesis-handout

organic-synthesis-handout - Organic Synthesis How can we...

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Organic Synthesis How can we form this? Substitution? No; the pi bond will break before Br contributes to a substitution reaction We could use hydrogenation of 1-bromo-1-butyne (provided only one of the pi bonds break) Performing an elimination on 1-bromo-2-butanol or 1-bromo-1-butanol would work best. CH CH 2 CH 2 CH 3 Br OH CH CH CH 2 CH 3 Br CH 2 CH CH 2 CH 3 CCC H 2 CH 3 Br CH 2 CH CH 2 CH 3 Br OH Best choice: only one product possible. How do we choose between reactions? Notice that their may be more than one way to form a particular compound The handout is an oversimplification … There are thousands of reaction mechanisms, many of which are very specific Considerations when choosing include … Yield (how much product forms) Potential for multiple products Ease of separating contaminating structures Type of isomer desired Economics: e.g. cost of starting materials Answers: 1, 2 1) An addition reaction involves breaking a double bond and adding two parts of a molecule across the bond
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This note was uploaded on 04/12/2011 for the course CHEM 1010 taught by Professor Marshall during the Spring '11 term at North Texas.

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