Propose structures for aromatic hydrocarbons that meet the following descriptions: (a) C 9 H 12 ; gives only one C 9 H 11 Br product on substitution of a hydrogen on the aromatic ring with bromine (b) C 10 H 14 ; gives only one C 10 H 13 Cl product on substitution of a hydrogen on the aromatic ring with chlorine (c) C 8 H 10 ; gives three C 8 H 9 Br products on substitution of a hydrogen on the aromatic ring with bromine (d) C 10 H 14 ; gives two C 10 H 13 Cl products on substitution of a hydrogen on the aromatic ring with chlorine

Question

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Answer 1

Textbook Question

Chapter 15.SE, Problem 23AP

Propose structures for aromatic hydrocarbons that meet the following descriptions:

(a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

(b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

(c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

(d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen on the aromatic ring with chlorine

Expert Solution

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8

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Will NBS (and heat or light) work for this reaction, or do we have to use Br2?

HAND DRAW

Predict the major products of the following organic reaction: Some important notes: Δ CN ? • Draw the major product, or products, of the reaction in the drawing area below. • If there aren't any products, because no reaction will take place, check the box below the drawing area instead. Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are enantiomers. ONO reaction. Click and drag to start drawing a structure.

Answer 2

Textbook Question

Chapter 15.SE, Problem 23AP

Propose structures for aromatic hydrocarbons that meet the following descriptions:

(a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

(b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

(c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

(d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen on the aromatic ring with chlorine

Expert Solution

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8

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Answer 3

Textbook Question

Chapter 15.SE, Problem 23AP

Propose structures for aromatic hydrocarbons that meet the following descriptions:

(a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

(b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

(c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

(d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen on the aromatic ring with chlorine

Expert Solution

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8

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Answer 4

Textbook Question

Chapter 15.SE, Problem 23AP

Propose structures for aromatic hydrocarbons that meet the following descriptions:

(a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

(b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

(c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

(d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen on the aromatic ring with chlorine

Expert Solution

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8

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Answer 5

Textbook Question

Answer 6

Textbook Question

Answer 7

Expert Solution

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Expert Solution

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Expert Solution

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Expert Solution

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8

Answer 8

Expert Solution

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Interpretation Introduction

a) C₉H₁₂; gives only one C₉H₁₁Br product on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen on the aromatic ring with bromine.

Answer 13

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 1

Answer 14

Explanation of Solution

The molecular formula of the compound is C₉H₁₂. Benzene ring accounts for six carbons. When the three carbons remaining are arranged as three methyl groups alternatively on the benzene ring the three hydrogens on the other three carbons become equivalent. Hence upon bromination, the hydrocarbon gives only one monosubstituted product.

Answer 15

Conclusion

A possible structure for the hydrocarbon with molecular formula C₉H₁₂ that gives only one monobromination product C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 2

Answer 16

Expert Solution

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Interpretation Introduction

b) C₁₀H₁₄; gives only one C₁₀H₁₃Cl product on substitution of a hydrogen on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring. Only one monosubstituted product will be obtained only if all the hydrogen atoms in the aromatic ring are equivalent.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product C₁₀H₁₃Cl on substitution of a hydrogen on the aromatic ring with chlorine is to be given.

Answer 21

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 3

Answer 22

Explanation of Solution

The molecular formula of the hydrocarbon is C₁₀H₁₄. Benzene ring accounts for six carbons. The remaining four carbons can be arranged as four methyl groups or as two ethyl groups on the benzene ring in four different ways as shown such that remaining hydrogen atoms become equivalent. Hence upon chlorination, the hydrocarbon will give only one monosubstituted product.

Answer 23

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives only one monochlorination product, C₁₀H₁₄Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 4

Answer 24

Expert Solution

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Interpretation Introduction

c) C₈H₁₀; gives three C₈H₉Br products on substitution of a hydrogen on the aromatic ring with bromine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products. C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three products, C₈H₉Br, on substitution of a hydrogen on the aromatic ring with bromine.

Answer 29

Answer to Problem 23AP

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products C₉H₁₁Br on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 5

Answer 30

Explanation of Solution

The molecular formula of the hydrocarbon is C₈H₁₀. Benzene ring accounts for six carbons. When the two carbons remaining are arranged as two methyl groups meta to each other or as an ethyl group on the benzene ring hydrogens on the other carbon atoms in the ring classify themselves into three different groups. Hence upon bromination, the hydrocarbon gives three monosubstituted products.

Answer 31

Conclusion

A possible structure for the hydrocarbon with molecular formula C₈H₁₀ that gives three monobromination products, C₉H₁₁Br, on substitution of a hydrogen atom on the aromatic ring with bromine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 6

Answer 32

Expert Solution

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Interpretation Introduction

d) C₁₀H₁₄; gives two C₁₀H₁₃Cl products on substitution of a hydrogen atom on the aromatic ring with chlorine

Interpretation:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two monochlorination products C₁₀H₁₃Cl on substitution of a hydrogen atom on the aromatic ring with chlorine is to be given.

Concept introduction:

All aromatic compounds are derivatives of benzene. The benzene ring accounts for six carbon atoms. The remaining carbons can be attached as alkyl group like methyl, ethyl etc. to the benzene ring.

To propose:

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₄ that gives two products, C₁₀H₁₃Cl, on substitution of a hydrogen on the aromatic ring with chlorine.

Answer 37

Answer to Problem 23AP

Possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 7

Answer 38

Explanation of Solution

The molecular formula of the compound is C₁₀H₁₄. Benzene ring accounts for six carbons. The four carbons remaining can be arranged as two ethyl groups or as an ethyl & two methyl groups or as propyl & methyl groups or as isopropyl & methyl groups on the benzene ring as shown so that the hydrogens on the other carbon atoms in the ring classify themselves into two different groups. Hence upon chlorination, the hydrocarbon gives two monosubstituted products.

Answer 39

Conclusion

A possible structure for the hydrocarbon with molecular formula C₁₀H₁₀ that gives two monobromination products, C₁₀H₁₃Cl, on substitution of a hydrogen atom on the aromatic ring with chlorine is

Organic Chemistry, Chapter 15.SE, Problem 23AP , additional homework tip 8