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7. Substitution Reactions

Nucleophilic Substitution

7. Substitution Reactions

Nucleophilic Substitution

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Remembering general patterns of reactions.

Remembering general patterns of reactions.

Johnny Betancourt

Nucleophiles and Electrophiles can react in Bronsted-Lowry Reactions.

Nucleophiles and Electrophiles can react in Bronsted-Lowry Reactions.

Johnny Betancourt

Nucleophiles and Electrophiles can react in Lewis Acid-Base Reactions.

Nucleophiles and Electrophiles can react in Lewis Acid-Base Reactions.

Johnny Betancourt

Nucleophiles and Electrophiles can react in Substitution Reactions.

Nucleophiles and Electrophiles can react in Substitution Reactions.

Johnny Betancourt

Predict the product

Predict the product

Johnny Betancourt

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Practice this topic

Multiple Choice

Given the curved arrow formalism, predict the products of the following reaction:

Multiple Choice

Based on the curved arrow formalism given, predict the products of this acid/base reaction.

Textbook Question

In contrast to the results of Assessment 13.18, when a secondary haloalkane is treated with sodium ethanethiolate, we predict formation of a thioether. How is this rationalized?

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Textbook Question

Predict the product of the following substitution/addition reactions involving phenoxides. [Because this problem represents a review of current and previous material, section numbers have been provided for your reference.]

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Textbook Question

The reaction of an alkyl chloride with potassium iodide is generally carried out in acetone to maximize the amount of alkyl iodide that is formed. Why does the solvent increase the yield of alkyl iodide?

(Hint: Potassium iodide is soluble in acetone, but potassium chloride is not.)

Textbook Question

The following functional-group interchange is a useful synthesis of aldehydes.

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(c) Explain why a nucleophilic reagent such as ethoxide adds to an alkyne more easily than it adds to an alkene.

Textbook Question

What is the product of the reaction of bromoethane with each of the following nucleophiles? a. CH3CH2CH2O− b. CH3C≡C−

Textbook Question

What is the product of the reaction of bromoethane with each of the following nucleophiles? c. (CH3)3N d. CH3CH2S-

Textbook Question

Cardura, a drug used to treat hypertension, is synthesized as shown here. + K2CO3—> A KOH—> B HCl, H2O—> Cardura + CH3OH a. Identify the intermediate (A) and show the mechanism for its formation.

Textbook Question

Strawberry growers have used large quantities of methyl bromide (b.p. 4 °C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43 °C) as a replacement for methyl bromide. 1. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? 2. Why is methyl iodide less likely to reach the stratosphere than methyl bromide?

Textbook Question

Which substitution reaction takes place more rapidly? a. CH3CH2Br + H2O or CH3CH2Br + HO−

Textbook Question

Draw all the products of the following reaction:

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