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Chapter 11: Problem 75

2-Butanone can be reduced to 2 -butanol by reagents such as lithium aluminum hydride \(\left(\mathrm{LiAlH}_{4}\right)\). (a) Write the formula of the product. Is it chiral? (b) In reality, the product does not exhibit optical activity. Explain.

Short Answer

Expert verified
The formula of the product of the reduction of 2-Butanone with LiAlH4 is C4H10O, corresponding to 2-Butanol. The product is chiral because it has a carbon atom joined to four different types of groups. However, it does not show optical activity because the reduction reaction likely produces a racemic mixture of the product, wherein the optical rotations induced by each enantiomer cancel each other out.

Step by step solution

01

The Reduction of 2-Butanone

The carbonyl compound 2-Butanone (also known as methyl ethyl ketone) reacts with Lithium Aluminium Hydride (LiAlH4), a reducing agent, to form an alcohol. This type of reaction is called a reduction. When 2-Butanone is reduced, the oxygen of the carbonyl group (C=O) receives two hydrogen atoms, converting the carbonyl group into the hydroxyl group (-OH) of an alcohol. So, the formula of the product is C4H10O.
02

Determining Chirality

The product of this reaction is 2-Butanol. It has a carbon atom that is connected to four different types of groups - a methyl group (-CH3), an ethyl group (-C2H5), a hydrogen atom (-H), and a hydroxyl group (-OH). This property, called chirality, makes it possible for the compound to exist in two mirror-image forms that cannot be superimposed on each other, also known as enantiomers. So, yes, 2-Butanol is chiral.
03

Explaining the Lack of Optical Activity

Typically, chiral compounds rotate plane-polarized light due to the different spatial arrangements of atoms in their molecules. However, in a mixture of an equal amount of both mirror-image forms (enantiomers) of a chiral molecule, the rotations of light caused by each form cancel each other out. This is called a racemic mixture. In this reaction, both enantiomers of 2-Butanol are likely produced in equal quantities, forming a racemic mixture that does not exhibit optical activity.

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