Alcohol Synthesis & Retrosynthesis of Target Molecules Worksheet

Provide a complete mechanism for both the formation of the cyclic acetal and then the hydrolysis of the acetal.  Pay close attention to details, including lone pairs, formal charges and the use of curved arrows.

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Alcohol Synthesis Homework

  1. Suggest two possible syntheses for the following target molecule (TM), starting with any aldehyde (start each synthesis with a different aldehyde). It may help to first consider a retrosynthesis of the TM.

CH3             OH

CH C CH2CH2CH2CH3

CH3

TM

  1. Show how you would synthesize pentanal (shown above) using the given starting materials:

1-pentene

1-hexene

1-pentyne

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