When 5-bromopentanal is treated with sodium borohydride, a compound is produced whose 13C NMR spectrum is shown here. In its IR spectrum, no absorption bands appear near 1700 cm-1 or above 3000 cm-1. Propose a mechanism to account for the formation of this product. NABH4 ? H. Br ETOH 200 150 100 50 Chemical shift (ppm) Fo

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
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When 5-bromopentanal is treated with sodium borohydride, a compound is produced whose 13C NMR spectrum is shown
here. In its IR spectrum, no absorption bands appear near 1700 cm-1 or above 3000 cm-1. Propose a mechanism to
account for the formation of this product.
NABH4
?
H.
Br
ETOH
200
150
100
50
Chemical shift (ppm)
Fo
Transcribed Image Text:When 5-bromopentanal is treated with sodium borohydride, a compound is produced whose 13C NMR spectrum is shown here. In its IR spectrum, no absorption bands appear near 1700 cm-1 or above 3000 cm-1. Propose a mechanism to account for the formation of this product. NABH4 ? H. Br ETOH 200 150 100 50 Chemical shift (ppm) Fo
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