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how would you properly balance this reaction?

how would you properly balance this reaction?

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter3: Organic Compounds: Alkanes And Their Stereochemistry
Section3.SE: Something Extra
Problem 49AP
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5 how would you properly balance this reaction?
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.
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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