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Chapter 12: Q12-46 (page 354)

Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400cm-1and M+=74in the mass spectrum?

Short Answer

Expert verified

Sodium borohydrides are selective reducing agents.Aldehydes and ketones get converted to alcohols when sodium borohydride functions as the reagent. Aldehydes yield primary alcohols and ketones yield secondary alcohols.

Step by step solution

01

Reaction of ketone with sodium borohydride

Sodium borohydrides are selective reducing agents.Aldehydes and ketones get converted to alcohols when sodium borohydride functions as the reagent. Aldehydes yield primary alcohols and ketones yield secondary alcohols.

02

Structure of the compound produced by reaction of 2-butanone with NaBH4

The m/z value of the product is 74. The IR spectrum shows that the compound has an IR absorption of 3400 cm- 1.

The ketone undergoes reduction with NaBH4forming an alcohol. The given compound 2-butanone undergoes reduction with NaBH4to form 2-butanol.

Reaction of 2-butanone withNaBH4

The IR absorption value at3400 cm- 1indicates the hydroxyl group in 2-btanol.

The molecular weight of the compound matches with the expected compound. Hence, the structure of the compound can be given as:

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Most popular questions from this chapter

Question: At what approximate positions might the following compounds show

IR absorptions?

(c)

How might you use IR spectroscopy to distinguish between the followingpairs of isomers?

(a) CH3 CH2 OH and CH3 OCH3

(b) Cyclohexane and 1 - hexene

(c) CH3 CH2 CO2 H and HOCH2 CH2 CHO

Predict the products of the following reactions:

Question: Grignard reagents undergo a general and very useful reaction with

ketones. Methylmagnesium bromide, for example, reacts with cyclohexanoneto yield a product with the formulaC7H14O . What is the structure of this product if it has an IR absorption at 3400cm-1?

Amino acids can be prepared by reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. Show how you would prepare alanine, CH3CH(NH2)CO2H, one of the twenty amino acids found in proteins, and propose a mechanism for acid-catalyzed conversion of the initial alkylation product to the amino acid.
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