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.

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