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Chapter 12: Q 46 E (page 385)

Question: Ketones undergo a reduction when treated with sodium borohydride, NaBH4.What is the structure of the compound produced by reactionof 2-butanone with NaBH4 if it has an IR absorption at 3400cm-1andM+=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

Step 2: 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 3400cm-1.

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

The IR absorption value at3400cm-1 indicates 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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