Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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how would you properly balance this reaction?

Transcribed Image Text:to form a primary alcohol. The aldehyde is citral, a component of essential oils
from a number of sources including lemon myrtle, lemongrass, lemon tea-tree
(70-90% of the essential oil), and to a lesser extent lemon, lime, and orange
(2-10% of the essential oil). Citral is a mixture of (E)-3,7-dimethyl-2,6-octadi-
enal (geranial) and (Z)-3,7-dimethyl-2,6-octadienal (neral). Reduction with
sodium borohydride produces a mixture of (E)-3,7-dimethyl-2,6-octadienol
(geraniol) and (Z)-3,7-dimethyl-2,6-octadienol (nerol) (Scheme 6-5). Notice
that the reaction depicted in Scheme 6-5 is not balanced, how would you prop-
erly balance this reaction? All of these compounds are fragrances used in the
perfume industry. Students should detect a noticeable difference in the odors
of citral and the geraniol/nerol mixture. Guanidinium chloride is added as
an electrophilic catalyst that activates the aldehyde to nucleophilic attack. The
reaction is remarkably regioselective because only the C=O bond is reduced,
leaving both C=C bonds untouched.
geranial
NABH4
geraniol
HO
NH, CI
H2N
NH2
THF/H20
neral
nerol
Scheme 6-5. NABH, reduction of citral to citrol.
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