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Chapter 22: Q37. (page 914)

Question: Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.

Short Answer

Expert verified

Answer

The order of reactivity of the given compounds is:

3>2>1

Step by step solution

01

Step-by-Step SolutionStep 1: Nucleophilic substitution reactions

Nucleophilic substitution reactions involve the reaction between an acyl group and a nucleophile.

The acyl groups connected to electron-deficient species are highly reactive towards nucleophilic substitution reactions.

02

Reactivity of the given compounds

Among the given compounds, the compound containing the carbonyl group connected to the chloride group is the most reactive, as chloride ion Cl-is a weak base and hence does not easily donate electrons.

Therefore, the carbonyl carbon of this compound is highly electron-deficient.

Among the other two compounds, the compound in which the carbonyl carbon is connected to the OH group is less electron-deficient than the one connected to the SH group, as -OHis more basic than -SH.

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Most popular questions from this chapter

Question: Draw the products of each reaction

a.

b.

Which carbonyl groups in the anticancer drug taxol (Section 5.5) will undergo nucleophilic addition and which will undergo nucleophilic substitution?

stereochemistry of the products of reduction depends on the reagent used,as you learned in Sections 20.5 and 20.6. With this in mind, how would you convert3,3-dimethylbutan-2-one [CH3COC(CH3)3] to: (a) racemic 3,3-dimethylbutan-2-ol[CH3CH(OH)C (CH3)3] ;(b) only (R)-3,3-dimethylbutan-2-ol; (c) only (S)-3,3-dimethylbutan-2-ol?

Question:Outline two different ways that butan-2-one can be prepared from a nitrile and a Grignard reagent.

What reagent is needed to convert (CH3)2CHCH2COCIinto each compound?

a.

b.

c.

d.
See all solutions

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