Acetal Protecting Group: Videos & Practice Problems

Give a synthetic scheme that would accomplish the following transformation. Use whatever reagents are needed.

Propose a synthetic scheme that would achieve the following transformation. Use whatever reagents are needed.

Determine the product formed when cyclobutanone reacts with butane-1,4-diol and p-toluenesulfonic acid.

Suggest a mechanism for the reaction below:

One of the compounds below exhibits reactivity, whereas the other remains unreactive with dilute aqueous acid. Provide the reaction mechanism of the reactive compound and explain why this mechanism does not apply to the unreactive compound.

i)

ii)

Identify the starting materials (including a carbonyl compound) required to form the following structure:

Provide the plausible major product of the reaction below.

Acetals are used as protecting groups for carbonyl compounds (aldehydes and ketones) and diols. A cyclic acetal is formed when a ketone or an aldehyde reacts with a diol. Determine the cyclic acetal produced when the compound below reacts with ethane-1,2-diol under acid catalysis.

Acetals are used as protecting groups for 1,2-diols and carbonyl compounds (aldehydes and ketones). Formation of an acetal using a diol as an alcohol yields a cyclic acetal. Provide the cyclic acetal formed when the following compound reacts with cyclobutane-1,2-diol under acid catalysis.

Draw a plausible synthesis that would efficiently carry out the following conversion. Use any necessary reagents.

Provide the steps necessary to complete the given synthesis. You may use any additional reagents that are required.

One of the following compounds exhibits reactivity, whereas the other remains unreactive with dilute aqueous acid. Propose a reaction mechanism of the reactive compound and explain why this mechanism does not apply to the unreactive compound.

i)

ii)