(a) Interpretation: How the given compound can be synthesized from two different alkenes is to be shown. Concept introduction: Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Question

When N,N-dimethylaniline is treated with bromine both the ortho and para products are observed. However when treated with a mixture of nitric acid and sulfuric acid only the meta product is observed. Explain these results and support your answer with the appropriate drawings *Hint amines are bases* N HNO3 H2SO4 N NO2 N Br2 N Br + N 8-8-8 FeBr3 Br

Answer 1

Question

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

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When N,N-dimethylaniline is treated with bromine both the ortho and para products are observed. However when treated with a mixture of nitric acid and sulfuric acid only the meta product is observed. Explain these results and support your answer with the appropriate drawings *Hint amines are bases* N HNO3 H2SO4 N NO2 N Br2 N Br + N 8-8-8 FeBr3 Br

Draw a mechanism that explains the formation of compound OMe SO3H 1. Fuming H2SO4

Consider the following two acid-base reactions: OH OHI Based on what you know about the compounds and their acidity, which direction would you expect both of these reactions to proceed? Show your reasoning. A pKa table has been provided in case you need it. Functional group Example pka CHA -50 Alkane -35 Amine : NH3 Alkyne RH 25 Water HO-H 169 16 10 Protonated amines NH 10 5 Carboxylic acids OH Hydrochloric acid HCI A chemist intends to run the following reaction on the three substrates shown below: H₂O R-CI product room temp. Cl Cl (1) (2) (3) They find one will react quickly, one slowly, and one will not react at all. Which is which, and why? HINT: What is the reaction they're trying to do? Does that mechanism tell you anything about why something would be favored?

Answer 2

Question

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

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Answer 3

Question

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

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Answer 4

Question

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

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Answer 5

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 6

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 7

Chapter 11, Problem 11.5P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 10

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 11

Interpretation Introduction

(c)

Interpretation:

How the given compound can be synthesized from two different alkenes is to be shown.

Concept introduction:

Bronsted acids add across a C - C double bond. The mechanism involves the electrophilic addition of the acid’s proton to the electron-rich π bond in step one. The proton adds to the less substituted carbon of the initial double bond so that the most substituted, and hence, the most stable carbocation forms. Step two is a coordination step in which the conjugate base forms a bond to the carbocation. The major product of an electrophilic addition of a Bronsted acid to an alkene is the one that proceeds through the more stable carbocation intermediate.

Answer 12

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Ch. 11 - Prob. 11.1P Ch. 11 - Prob. 11.2P Ch. 11 - Prob. 11.3P Ch. 11 - Prob. 11.4P Ch. 11 - Prob. 11.5P Ch. 11 - Prob. 11.6P Ch. 11 - Prob. 11.7P Ch. 11 - Prob. 11.8P Ch. 11 - Prob. 11.9P Ch. 11 - Prob. 11.10P

Solution Summary: The author explains how Bronsted acids add across a C - C double bond. The proton adds to the less substituted carbon of the initial bond so that the most stable carboc

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