Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 7.54P
Interpretation Introduction

(a)

Interpretation: The given species are to be arranged in order of increasing nucleophilicity.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom. The good nucleophiles are strong base whose conjugate acids have high pKa value.

Expert Solution
Check Mark

Answer to Problem 7.54P

The order of increasing nucleophilicity is OH<NH2<CH3

Explanation of Solution

On moving right to left across a row in periodic table, nucleophilicity as well as the basicity increases. Therefore, the order of increasing nucleophilicity is OH<NH2<CH3

Conclusion

The order of increasing nucleophilicity is OH<NH2<CH3.

Interpretation Introduction

(b)

Interpretation: The given species are to be arranged in order of increasing nucleophilicity.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom. The good nucleophiles are strong base whose conjugate acids have high pKa value.

Expert Solution
Check Mark

Answer to Problem 7.54P

The order of increasing nucleophilicity is H2O<OH<SH

Explanation of Solution

The size of SH is greater than that of OH. Therefore, it is more nucleophilic because the nucleophilicity increases with increase in the size of the anion. OH is more nucleophilic than its conjugate acid H2O. Therefore, the order of increasing nucleophilicity is H2O<OH<SH

Conclusion

The order of increasing nucleophilicity is H2O<OH<SH.

Interpretation Introduction

(c)

Interpretation: The given species are to be arranged in order of increasing nucleophilicity.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom. The good nucleophiles are strong base whose conjugate acids have high pKa value.

Expert Solution
Check Mark

Answer to Problem 7.54P

The order of increasing nucleophilicity is CH3CO2<CH3CH2O<CH3CH2S

Explanation of Solution

A solvent in which hydrogen atom is bonded to electronegative O or N atom is termed as polar protic solvent. Methanol is a polar protic solvent. In polar protic solvent on moving down the group, basicity increases because the size of anion increases. Sulfur lies below oxygen atom in a periodic table. Thus, nucleophilicity of CH3CH2S is higher. The conjugate acid of good nucleophile has high pKa value. The pKa value of conjugate acid of CH3CO2 has higher value than the pKa value of conjugate acid of CH3CH2O. Therefore, the order of increasing nucleophilicity is CH3CO2<CH3CH2O<CH3CH2S.

Conclusion

The order of increasing nucleophilicity is CH3CO2<CH3CH2O<CH3CH2S.

Interpretation Introduction

(d)

Interpretation: The given species are to be arranged in order of increasing nucleophilicity.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom. The good nucleophiles are strong base whose conjugate acids have high pKa value.

Expert Solution
Check Mark

Answer to Problem 7.54P

The order of increasing nucleophilicity is CH3SH<CH3OH<CH3NH2.

Explanation of Solution

The nucleophilicity and basicity are directly related to each other in polar aprotic solvent. Acetone is a polar aprotic solvent.

On moving down the group in a periodic table and left to right in a period, basicity decreases and hence, nucleophilicity decreases. Sulfur lies below oxygen atom and nitrogen lies left to oxygen atom in a periodic table. Thus, the order of increasing nucleophilicity is CH3SH<CH3OH<CH3NH2.

Conclusion

The order of increasing nucleophilicity is CH3SH<CH3OH<CH3NH2.

Interpretation Introduction

(e)

Interpretation: The given species are to be arranged in order of increasing nucleophilicity.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom. The good nucleophiles are strong base whose conjugate acids have high pKa value.

Expert Solution
Check Mark

Answer to Problem 7.54P

The order of increasing nucleophilicity is Cl<F<OH.

Explanation of Solution

The nucleophilicity and basicity are directly related to each other in polar aprotic solvent. Acetone is a polar aprotic solvent.

On moving down the group in a periodic table and left to right in a period, basicity decreases and hence, nucleophilicity decreases. Chlorine lies below fluorine atom and nitrogen lies left to fluorine in a periodic table. Thus, the order of increasing nucleophilicity is Cl<F<OH.

Conclusion

The order of increasing nucleophilicity is Cl<F<OH.

Interpretation Introduction

(f)

Interpretation: The given species are to be arranged in order of increasing nucleophilicity.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom. The good nucleophiles are strong base whose conjugate acids have high pKa value.

Expert Solution
Check Mark

Answer to Problem 7.54P

The order of increasing nucleophilicity is F<HS<Cl.

Explanation of Solution

A solvent in which hydrogen atom is bonded to electronegative O or N atom is termed as polar protic solvent. Methanol is a polar protic solvent. In polar protic solvent, on moving down the group and right to left in a periodic table, basicity increases because the size of anion increases. Thus, the order of increasing nucleophilicity is F<HS<Cl.

Conclusion

The order of increasing nucleophilicity is F<HS<Cl.

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Chapter 7 Solutions

Organic Chemistry-Package(Custom)

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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