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Organic Chemistry 2

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Moderate

Multistep Synthesis with Acetal Protecting Groups

ORGO2-0X9IJV

Acetal protecting group methodology is commonly employed when a reagent that is reactive to aldehydes/ketones needs to be used in the presence of an aldehyde or ketone functional group, but the desired reaction is at some other place in the molecule.

Acetal protecting groups are especially useful because they are easily installed with mild acid, inert to nucleophilic reagents, and easily removed by treatment with mild aqueous acid. The questions below relate to the following sequence of reactions depicted below.

Created for Albert.io. Copyright 2016. All rights reserved.

The main reason that one cannot treat compound A with $LiAlH_4$ to form Compound D directly is

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Compound B is structure

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Compound C is structure

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Structure Choices for Compounds B and C:

Created for Albert.io. Copyright 2016. All rights reserved.