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Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Chemistry MCQ


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10 Questions MCQ Test - Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent

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Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 1

Which of the following reactions does not give the product indicated?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 1

Reaction (b) with two equivalents of the Grignard reagent and the ester followed by an aqueous workup gives a tertiary alcohol, but it is 1,1- diphenylethanol (CH3CPh2OH).

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 2

Which of the following reactions does not give the product indicated?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 2

In reaction (d), the reduction of the amide with UAIH4 leads to the amine, MeOCH2CH2NMe2.

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Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 3

Which compound does not give a tertiary alcohol upon reaction with ethylmagnesium bromide in ether followed by a workup with aqueous ammonium chloride?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 3

Esters (other than formates) and ketones generally react with Grignard reagents to give tertiary alcohols, but aldehydes give secondary alcohols.

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 4

Which of the following reactions does not give a primary alcohol?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 4

In reaction (a), the ester cannot be reduced with NaBH4.

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 5

Which of the following carbonyl compounds does not give 2-methylpentan-2-ol upon reaction with methylmagnesium iodide in ether followed by a workup with aqueous ammonium chloride?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 5

Draw structures of the carbonyl compounds first, then identify the products of their reactions with the Grignard reagent.

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 6

Which of the following incorrectly represents the flow of electrons in the hydride reduction of an aldehyde with NaBH4?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 6

In this reaction, the B-H bond provides the electron pair which forms the new bond, so this is where the curly arrow should start; the formal negative charge on B does not represent a lone pair. 

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 7

Which is the reduction product of the following compound with LiAIH4 in ether followed by aqueous workup?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 7

LiAIH4 is sufficiently reactive to reduce both ketone and ester groups: the ester part initially becomes the conjugate base of a hemiacetal which forms a ring-opened aldehydic alkoxide in the reaction mixture, and the aldehyde residue is then reduced further; acidification gives the triol shown.

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 8

Which is the main reduction product of the following compound with NaBH4 in methanol?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 8

The substrate is a keto ester and NaBH4 can reduce only the ketone carbonyl.

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 9

Which is the main reduction product of the following compound with UAIH4 in ether followed by an aqueous workup?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 9

LiAIH4 is a powerful hydride donor which generally reduces all types of carbonyl functional groups.

Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 10

Which is the main reduction product of the following compound with NaBH4 in methanol?

Detailed Solution for Test: Solved Practice Questions on LiAlH4, NaBh4 & grignard reagent - Question 10

NaBH4 is a mild hydride donor which, in general, reduces aldehydes and ketones but not esters or amides.

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