Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 7, Problem 7.20P
Interpretation Introduction

(a)

Interpretation: The change that occurs to the rate of an SN2 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.

Expert Solution
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Answer to Problem 7.20P

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

Explanation of Solution

The rate of SN2 reaction depends upon the concentration of reactant (alkyl halide, RX) and incoming nucleophile (Nu).

The rate of SN2 reaction is expressed as,

Rate=k[RX][Nu]

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

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

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.

Interpretation Introduction

(b)

Interpretation: The change that occurs to the rate of an SN2 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.

Expert Solution
Check Mark

Answer to Problem 7.20P

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

Explanation of Solution

The rate of SN2 reaction depends upon the concentration of reactant (alkyl halide, RX) and incoming nucleophile (Nu).

The rate of SN2 reaction is expressed as,

Rate=k[RX][Nu]

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

Rate=k[3RX][3Nu]=9(k[RX][Nu])

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

Conclusion

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

Interpretation Introduction

(c)

Interpretation: The change that occurs to the rate of an SN2 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.

Expert Solution
Check Mark

Answer to Problem 7.20P

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 SN2 reaction depends upon the concentration of reactant (alkyl halide, RX) and incoming nucleophile (Nu).

The rate of SN2 reaction is expressed as,

Rate=k[RX][Nu]

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][Nu]=12(k[RX][Nu])

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.

Interpretation Introduction

(d)

Interpretation: The change that occurs to the rate of an SN2 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.

Expert Solution
Check Mark

Answer to Problem 7.20P

The rate of the reaction remains unchanged when the concentration of [RX] is halved and [Nu] is doubled.

Explanation of Solution

The rate of SN2 reaction depends upon the concentration of reactant (alkyl halide, RX) and incoming nucleophile (Nu).

The rate of SN2 reaction is expressed as,

Rate=k[RX][Nu]

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

Rate=k[12×RX][2Nu]=k[RX][Nu]

Therefore, the rate of the reaction remains unchanged when the concentration of [RX] is halved and [Nu] is doubled.

Conclusion

The rate of the reaction remains unchanged 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 - Prob. 7.12PCh. 7 - Does the equilibrium favor the reactants or...Ch. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Classify each solvent as protic or aprotic. a. b....Ch. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Draw an energy diagram for the reaction in Problem...Ch. 7 - Draw the product of each SN2 reaction and indicate...Ch. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 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. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Which alkyl halide in each pair reacts faster in...Ch. 7 - Prob. 7.32PCh. 7 - Problem 7.30 For each alkyl halide and...Ch. 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 - Prob. 7.40PCh. 7 - Prob. 7.41PCh. 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....Ch. 7 - Prob. 7.45PCh. 7 - Classify each alkyl halide in Problem 7.44 as 1 ,...Ch. 7 - Draw the eight constitutional isomers having the...Ch. 7 - Prob. 7.48PCh. 7 - Draw the substitution product that results when...Ch. 7 - Draw the products of each nucleophilic...Ch. 7 - Prob. 7.51PCh. 7 - Rank the species in each group in order of...Ch. 7 - Which of the following nucleophilic substitution...Ch. 7 - Prob. 7.54PCh. 7 - Prob. 7.55PCh. 7 - Prob. 7.56PCh. 7 - 7.53 Consider the following reaction. Draw a...Ch. 7 - Prob. 7.58PCh. 7 - Prob. 7.59PCh. 7 - Draw the products of each SN2 reaction and...Ch. 7 - Prob. 7.61PCh. 7 - Prob. 7.62PCh. 7 - Prob. 7.63PCh. 7 - Consider the following SN1 reaction. a.Draw a...Ch. 7 - Prob. 7.65PCh. 7 - Prob. 7.66PCh. 7 - Draw the products of each SN1 reaction and...Ch. 7 - Prob. 7.68PCh. 7 - Prob. 7.69PCh. 7 - Diphenhydramine, the antihistamine in Benadryl,...Ch. 7 - Draw a stepwise, detailed mechanism for the...Ch. 7 - When a single compound contains both a nucleophile...Ch. 7 - Prob. 7.73PCh. 7 - Prob. 7.74PCh. 7 - Draw a stepwise, detailed mechanism f or the...Ch. 7 - Prob. 7.76PCh. 7 - Fill in the appropriate reagent or starting...Ch. 7 - Devise a synthesis of each compound from an alkyl...Ch. 7 - Prob. 7.79PCh. 7 - Suppose you have compounds A-D at y our disposal....Ch. 7 - Prob. 7.81PCh. 7 - Prob. 7.82PCh. 7 - Prob. 7.83PCh. 7 - Prob. 7.84PCh. 7 - 7.80 As we will learn in Chapter 9, an epoxide is...Ch. 7 - Prob. 7.86PCh. 7 - In some nucleophilic substitutions under SN1...
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