What are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product?What if α-Pinene is treated with peroxy acid + THF? 8.17 a-Pinene can be isolated from pine resin and is a primary constituent of turpentine(paint thinner). Both enantiomers of a-pinene are naturally occurring. To determine the enan-tiomeric excess (% ee) of a-pinene in various spruce trees, the isolated a-pinene was modi-fied by hydroboration-oxidation as shown below for the (-)-enantiomer. In the first step,diborane (B2H&) was used as an alternative to BH3• THF to achieve hydroboration of thealkene. Since hydroboration can take place from either face of the alkene, there are twopossible diastereomeric products, but the major product results from attack on the less hin-dered face. Draw both products and predict which is the major diastereomer formed.CH3H3C-1) B2H62) H2O2, NaOHCH3()-a-Pinene

Answered: What are the possible products when…

What are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product? What if α-Pinene is treated with peroxy acid + THF?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.SE: Something Extra

Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...

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Concept explainers

Alkynes

Alkynes are organic compounds that contain at least one triple bond between carbon-carbon atoms. They are a series of unsaturated compounds with a general molecular formula, CnH2n-2.

Question

What are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product?

What if α-Pinene is treated with peroxy acid + THF?

8.17 a-Pinene can be isolated from pine resin and is a primary constituent of turpentine
(paint thinner). Both enantiomers of a-pinene are naturally occurring. To determine the enan-
tiomeric excess (% ee) of a-pinene in various spruce trees, the isolated a-pinene was modi-
fied by hydroboration-oxidation as shown below for the (-)-enantiomer. In the first step,
diborane (B2H&) was used as an alternative to BH3• THF to achieve hydroboration of the
alkene. Since hydroboration can take place from either face of the alkene, there are two
possible diastereomeric products, but the major product results from attack on the less hin-
dered face. Draw both products and predict which is the major diastereomer formed.
CH3
H3C-
1) B2H6
2) H2O2, NaOH
CH3
()-a-Pinene

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