Quiz - Retrosynthetic strategies - 2 | Strategies for Synthesis and Retrosynthesis

Organic Chemistry 1 - Quiz - Retrosynthetic strategies - 2


Which of the following alcohol protecting groups is most suitable when ultimate removal must be acid sensitive?

Methoxymethyl ether (MOM) protecting group is suitable when the deprotection must be acid sensitive as it can be removed under mildly acidic conditions without affecting acid-labile functional groups.


What is a key consideration when selecting a carbonyl protecting group during the synthesis of a ketone with several nucleophilic sites?

Compatibility of the protecting group with subsequent reaction conditions is crucial to ensure that the protecting group stays intact during other transformations and does not interfere with the site of reactivity.


During retrosynthetic analysis of a tertiary alcohol, you identify a need for stereoselective synthesis. Which of the following strategies aligns with this objective?

The use of chiral auxiliaries in the synthesis of tertiary alcohols can induce stereoselectivity, leading to the preferential formation of one enantiomer over the other.


How can the retrosynthetic principle of 'simplifying to the most basic skeleton' be applied when approaching molecules with multiple ether functional groups?

Cleaving the ether bonds to generate simpler alcohol intermediates allows for the retrosynthetic simplification of complex molecules and the identification of a synthetic route that builds complexity stepwise.


Which retosynthesis strategy is best to protect a carbonyl group while performing a highly nucleophilic addition on another functional group of the same molecule?

Acetals and ketals serve as excellent carbonyl-protecting groups that can withstand highly nucleophilic conditions, making them appropriate for selective reactions on the same molecule.


What consideration is primarily taken into account when deciding to use TBDMS as an alcohol protecting group in a multistep synthesis involving Grignard reagents?

TBDMS is stable under the conditions required for Grignard reactions, which often involve strong nucleophiles and bases, thus, it will not interfere or be removed during those steps.


What is the retrosynthetic analysis step that best describes breaking down a molecule into a simpler precursor with an alkyne as a synthetic handle?

Alkyne to ketone/aldehyde transposition is a useful retrosynthetic step as alkynes are versatile handles that can be converted to ketones or aldehydes, providing a platform for further functionalization.


In designing a synthesis for a molecule containing multiple protected groups, which of the following aspects is most vital to the deprotection strategy?

Orthogonal deprotection conditions are essential in complex syntheses, as they allow the selective removal of one protecting group at a time without affecting others.