a) 1 mol Br 2 in CH 2 Cl 2 Interpretation: The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH 2 Cl 2 are to be given. Concept introduction: Conjugated dienes are treated with bromine in CH 2 Cl 2 undergo both 1,2 and 1,4 addition of bromine to yield different products. To give: The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH 2 Cl 2 .

Question

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Answer 1

Question

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 18

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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

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Answer 2

Question

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 18

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 18

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Answer 4

Question

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 18

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Answer 5

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 18

Answer 6

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Answer 7

Chapter 14.SE, Problem 27AP

Interpretation Introduction

a) 1 mol Br₂ in CH₂Cl₂

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are to be given.

Concept introduction:

Conjugated dienes are treated with bromine in CH₂Cl₂ undergo both 1,2 and 1,4 addition of bromine to yield different products.

To give:

The product expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂.

Answer 8

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of bromine in CH₂Cl₂ it yields 3,6-dibromocyclohexene by 1,4 addition and 3,4-dibromocyclohexene by 1,2 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 2

Answer 13

Conclusion

The products expected to be formed when 1,3-cyclohexadiene reacts with one mole of bromine in CH₂Cl₂ are 3,6-dibromocyclohexene and 3,4-dibromocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 3

Answer 14

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Answer 15

Interpretation Introduction

b) O₃ followed by Zn

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Concept introduction:

Alkenes and dienes form ozonide when treated with ozone. The addition of ozone takes place to the double bonds. On reduction the ozonide cleaves and an oxygen atom becomes doubly bonded to each of the original alkene carbons to yield carbonyl compounds as products.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc is to be given.

Answer 16

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

Ozone adds to both the double bonds in 1,3-cyclohexadiene to form an ozonide. When treated with Zn and acetic acid the ozonide breaks to yield carbonyl compounds. The carbons that have oxygen in the products are joined through double bonds in the reactant.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 5

Answer 21

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with ozone followed by zinc are glyoxal and succindialdehyde.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 6

Answer 22

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Answer 23

Interpretation Introduction

c) 1 mol HCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl in ether is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted cyclic conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is to be given.

Answer 24

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 7

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

Both 1,2 and 1,4 addition of HCl to 1,3-cyclohexadiene leads to the formation of the same product, 3-chlorocyclohexene, as it is an unsubstituted conjugated 1,3-diene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 8

Answer 29

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with one mole of HCl is 3-chlorocyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 9

Answer 30

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Answer 31

Interpretation Introduction

d) 1 mol DCl in ether

Interpretation:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are to be given.

Concept introduction:

Conjugated dienes when treated with one mole of DCl in ether undergo both 1,2 and 1,4 addition of DCl to yield different products.

To give:

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl.

Answer 32

Expert Solution

Answer to Problem 27AP

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 10

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

1,3-cyclohexadiene is a conjugated diene. When treated with one mole of DCl it yields 3-chloro-4-deuteratedcyclohexen by 1,2 addition 3-chloro-6-deuteratedcyclohexene by 1,4 addition reaction.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 11

Answer 37

Conclusion

The products expected to be formed when 1,3-cyclohexadiene is treated with one mole of DCl are 3-chloro-4-deuteratedcyclohexene and 3-chloro-6-deuteratedcyclohexene.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 12

Answer 38

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Answer 39

Interpretation Introduction

e) 3-Buten-2-one (H₂C=CHCOCH₃)

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is to be given.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1,4 addition of the dienophile into the diene through a cyclic transition state. During the reaction the diene and dienophile orient themselves on top of one another and so an endo product results.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one.

Answer 40

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 13

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

The diene, 1,3-cyclohexadiene and the dienophile 3-buten-2-one arrange themselves one on the top of the other and react through the formation of a cyclic six member transition state to yield the endo product.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 14

Answer 45

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with 3-buten-2-one is

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 15

Answer 46

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17

Conclusion

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 18

Answer 47

Interpretation Introduction

f) Excess O_sO₄, followed by NaHSO₃

Interpretation:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is to be given.

Concept introduction:

The reaction given involves hydroxylation of the double bonds in the diene. When a diene is treated with OsO₄, a single step addition of OsO₄ to each of the double bonds takes place to give a cyclic osmate. The cyclic osmate gets cleaved when treated with NaHSO₃ yields a tetraol.

To give:

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃.

Answer 48

Expert Solution

Answer to Problem 27AP

The product expected to be formed when 1,3-cyclohexadiene is treated with excess OsO₄ and then with NaHSO₃ is cyclohexane-1,2,3,4-tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 16

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

When 1,3-cyclohexadiene is treated with excess OsO₄ the addition of OsO₄ takes place to both the double bonds in it. The addition occurs with syn stereochemistry to yield a cyclic osmate. The cyclic osmate then gets cleaved when treated with NaHSO₃ to yield the tetraol.

Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th, Chapter 14.SE, Problem 27AP , additional homework tip 17