Answered: Identify the stereogenic carbon in (S)-…

Identify the stereogenic carbon in (S)- and (R)-limonene, rank the substituents around it and rationalize the assignment of their stereochemical configurations.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter18: Aromaticity

Section: Chapter Questions

Problem 3CTQ

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

Identify the stereogenic carbon in (S)- and (R)-limonene, rank the substituents around it and rationalize the assignment of their stereochemical configurations.

1. Identify the stereogenic carbon in (S)- and
(R)-limonene, rank the substituents around it
and rationalize the assignment of their
stereochemical
configurations. Hint: When
ranking carbons that have multiple bonds,
consider the bolded carbon of C=C being
connected to 2 carbons and the bolded
carbon of C=C being connected to 3 carbons.

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