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What is the mechanism of the reduction of organic acids with borane? Borane reductions don't work well with electron deficient carbonyl groups. Why is that so, and how isn't the carboxyl group an electron deficient group?

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What is the mechanism of the reduction of organic acids with borane?

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Source:
Henry Rzepa. Chemistry with a twist. Mechanism of the reduction of a carboxylic acid by borane: revisited and revised. October 16th, 2011. http://www.ch.imperial.ac.uk/rzepa/blog/?p=5114
DOI: 10.15200/winn.142795.57029 provided by The Winnower, a DIY scholarly publishing platform.

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    $\begingroup$ but I see an ester in your answer. $\endgroup$ – RE60K Apr 27 '15 at 6:51
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    $\begingroup$ I think quoting that R=H is a possibility from the original source might clear up the confusion. $\endgroup$ – ChemExchange Apr 30 '15 at 10:41

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