What do you expect the most prominent features to be in the IR spectra of the reactant and product? Compare the relative base strengths of the hydride ion and the alkoxide ion, and explain what each of the workup steps (i.e. after the initial reaction with NaBH4) does.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy
Section12.SE: Something Extra
Problem 37AP: Assume that you are carrying out the base-induced dehydrobromination of 3-bromo-3-methylpentane...
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borohydride reduction

What do you expect the most prominent features to be in the IR spectra of the reactant and product?

Compare the relative base strengths of the hydride ion and the alkoxide ion, and explain what each of the workup steps (i.e. after the initial reaction with NaBH4) does.

 

 

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500 L of 1-naphthaldehyde was added to a 10 mL round bottom flask along with 3.0 mL of methanol. This mixture was stirred until the aldehyde was dissolved in the methanol. This flask was placed in an ice bath and 100 mg of NaBH4 was added in 2-3 portions (weighed out in a small tube) over a few minutes. Stop the addition if excessive bubbling is observed. The flask is removed from the ice bath and is allowed to come to room temperature and stirred for 10 minutes. The borate ester is hydrolyzed by treating with 2.5 mL of 3 M NaOH. The resultant solution may be cloudy. Add 1-2 mL of water until you see a defined upper organic layer. Remove as much of the top layer as possible and place in a small clean dry test tube. Extract the remaining solution twice with dichloromethane (2x 1mL) removing the lower organic layer each time and combining it with the top layer originally removed. Dry the dichloromethane extracts by filtering the solution through a pipette containing anhydrous magnesium sulfate and sand. Filter this mixture into a clean dry beaker and evaporate the dichloromethane solution in the hood using a hot plate set to very low heat and agitating the mixture frequently.

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