Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 7, Problem 7.23P

What happens to the rate of an S N 1 reaction under each of the following conditions?

a. [ RX ] is tripled, and [ Nu ] stays the same.

b. Both [ RX ] and [ Nu ] are tripled.

c. [ RX ] is halved, and [ Nu ] stays the same.

d. [ RX ] is halved, and [ Nu ] is doubled.

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The change that occurs to the rate of an SN1 reaction when [RX] is tripled and [Nu] stays the same is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.23P

The rate of the reaction increases by three times when the concentration of [RX] is tripled.

Explanation of Solution

The rate of SN1 reaction depends upon the concentration of reactant (alkyl halide, RX) only. The concentration of incoming nucleophile (Nu) has no effect on the rate of SN1 reaction.

The rate of SN1 reaction is expressed as,

Rate=k[RX]

According the given statement, the concentration of [RX] is tripled. Hence, the rate of the reaction is,

Rate=k[3RX]=3(k[RX])

Therefore, the rate of the reaction increases by three times when the concentration of [RX] is tripled.

Conclusion

The rate of the reaction increases by three times when the concentration of [RX] is tripled.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The change that occurs to the rate of an SN1 reaction when both [RX] and [Nu] are tripled is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.23P

The rate of the reaction increases by three times when the concentration of both [RX] and [Nu] is tripled.

Explanation of Solution

The rate of SN1 reaction depends upon the concentration of reactant (alkyl halide, RX) only. The concentration of incoming nucleophile (Nu) has no effect on the rate of SN1 reaction.

The rate of SN1 reaction is expressed as,

Rate=k[RX]

According the given statement, the concentration of both [RX] and [Nu] is tripled. Hence, the rate of the reaction is,

Rate=k[3RX]=3(k[RX])

Therefore, the rate of the reaction increases by three times when the concentration of both [RX] and [Nu] is tripled.

Conclusion

The rate of the reaction increases by three times when the concentration of both [RX] and [Nu] is tripled.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The change that occurs to the rate of an SN1 reaction when [RX] is halved and [Nu] stays the same is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.23P

The rate of the reaction decreases by half when the concentration of [RX] is halved and [Nu] stays the same.

Explanation of Solution

The rate of SN1 reaction depends upon the concentration of reactant (alkyl halide, RX) only. The concentration of incoming nucleophile (Nu) has no effect on the rate of SN1 reaction.

The rate of SN1 reaction is expressed as,

Rate=k[RX]

According the given statement, the concentration of both [RX] is halved and [Nu] stays the same. Hence, the rate of the reaction is,

Rate=k[12×RX]=12(k[RX])

Therefore, the rate of the reaction decreases by half when the concentration of [RX] is halved and [Nu] stays the same.

Conclusion

The rate of the reaction decreases by half when the concentration of [RX] is halved and [Nu] stays the same.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The change that occurs to the rate of an SN1 reaction when [RX] is halved and [Nu] is doubled is to be predicted.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Answer to Problem 7.23P

The rate of the reaction decreases by half when the concentration of [RX] is halved and [Nu] is doubled.

Explanation of Solution

The rate of SN1 reaction depends upon the concentration of reactant (alkyl halide, RX) only. The concentration of incoming nucleophile (Nu) has no effect on the rate of SN1 reaction.

The rate of SN1 reaction is expressed as,

Rate=k[RX]

According the given statement, the concentration of both [RX] is halved and [Nu] is doubled. Hence, the rate of the reaction is,

Rate=k[12RX]=12k[RX]

Therefore, The rate of the reaction decreases by half when the concentration of [RX] is halved and [Nu] is doubled.

Conclusion

The rate of the reaction decreases by half when the concentration of [RX] is halved and [Nu] is doubled.

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Chapter 7 Solutions

Organic Chemistry

Ch. 7 - Prob. 7.11PCh. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.13PCh. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.15PCh. 7 - Prob. 7.16PCh. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.21PCh. 7 - Prob. 7.22PCh. 7 - What happens to the rate of an SN1 reaction under...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Classify each carbocation as 1,2, or 3. a. b. c....Ch. 7 - Prob. 7.26PCh. 7 - Prob. 7.27PCh. 7 - Prob. 7.28PCh. 7 - Prob. 7.29PCh. 7 - Problem 7.30 For each alkyl halide and...Ch. 7 - Prob. 7.31PCh. 7 - Prob. 7.32PCh. 7 - Prob. 7.33PCh. 7 - Prob. 7.34PCh. 7 - Prob. 7.35PCh. 7 - Prob. 7.36PCh. 7 - Prob. 7.37PCh. 7 - Prob. 7.38PCh. 7 - Prob. 7.39PCh. 7 - Give the IUPAC name for each compound, including...Ch. 7 - Draw the products formed when each alkyl halide is...Ch. 7 - Give the IUPAC name for each compound. a. c. e. b....Ch. 7 - Prob. 7.43PCh. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Which compound in each pair has the higher boiling...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.47PCh. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Rank the species in each group in order of...Ch. 7 - Prob. 7.51PCh. 7 - Prob. 7.52PCh. 7 - 7.53 Consider the following reaction. Draw a...Ch. 7 - Prob. 7.54PCh. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.56PCh. 7 - Prob. 7.57PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - 7.59 Pick the reactant or solvent in each part...Ch. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.61PCh. 7 - Prob. 7.62PCh. 7 - Prob. 7.63PCh. 7 - Fluticasone, the chapter-opening molecule, can be...Ch. 7 - Prob. 7.65PCh. 7 - 7.66 Diphenhydramine, the antihistamine in...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.69PCh. 7 - Prob. 7.70PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.72PCh. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Muscalure, the sex pheromone of the common...Ch. 7 - Prob. 7.77PCh. 7 - Prob. 7.78PCh. 7 - Draw a stepwise mechanism for the following...Ch. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.81PCh. 7 - In some nucleophilic substitutions under SN1...
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