Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 11, Problem 11.43P
Interpretation Introduction

(a)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The addition of an electrophile to an alkyne is followed by Markovnikoff’s rule and anti-stereoselectivity.

The addition of a halogen to an alkyne chain leads to the formation of corresponding alkene or alkane. The reaction which includes the addition of bromine atoms to the alkyne chain is known as bromination. Bromination can be done by using the reagents like HBr or Br2. The reaction which includes the addition of chlorine atoms to the alkyne chain is known as chlorination. Chlorination can be done by using the reagents like HCl or Cl2.

Expert Solution
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Answer to Problem 11.43P

The product that is formed by the reaction is 2,2dibromoheptane.

Explanation of Solution

The reaction of hept1yne with two equivalents of HBr is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  1

Figure 1

The reaction of hept1yne with two equivalents of HBr results in the formation of 2,2dibromoheptane. In this reaction, the negatively charged bromide ions from two equivalents of HBr get substituted on the highly substituted carbon atom of hept1yne to form the desired dihalide product.

Conclusion

The product that is formed by the reaction is 2,2dibromoheptane.

Interpretation Introduction

(b)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The addition of an electrophile to an alkyne is followed by Markovnikoff’s rule and anti-stereoselectivity.

The addition of a halogen to an alkyne chain leads to the formation of corresponding alkene or alkane. The reaction which includes the addition of bromine atoms to the alkyne chain is known as bromination. Bromination can be done by using the reagents like HBr or Br2. The reaction which includes the addition of chlorine atoms to the alkyne chain is known as chlorination. Chlorination can be done by using the reagents like HCl or Cl2.

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Answer to Problem 11.43P

The product that is formed by the reaction is 1,1,2,2tetrachloro3,3dimethylbutane.

Explanation of Solution

The reaction of 3,3dimethylbut1yne with two equivalents of Cl2 is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  2

Figure 2

The reaction of 3,3dimethylbut1yne with two equivalents Cl2 results in the formation of 1,1,2,2tetrachloro3,3dimethylbutane. In this reaction, the negatively charged chloride ions from two equivalents of Cl2 get substituted on the highly substituted carbon atom of 3,3dimethylbut1yne to form the desired tetrahalide product.

Conclusion

The product that is formed by the reaction is 1,1,2,2tetrachloro3,3dimethylbutane.

Interpretation Introduction

(c)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The addition of a halogen to an alkyne chain leads to the formation of corresponding alkene or alkane. The reaction which includes the addition of bromine atoms to the alkyne chain is known as bromination.

The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

Expert Solution
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Answer to Problem 11.43P

The product that is formed by the reaction is 1,2diphenylethyne.

Explanation of Solution

The reaction of 1,2diphenylethene with one equivalent of Cl2 is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  3

Figure 3

The reaction of 1,2diphenylethene with one equivalent Cl2 results in the formation of 1,2dichloro1,2diphenylethane. In this reaction, the negatively charged chloride ions from one equivalents of Cl2 get substituted on the highly substituted carbon atom of 3,3dimethylbut1yne to form the desired dihalide product.

The reaction of 1,2dichloro1,2diphenylethane with two equivalents of NaNH2 is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  4

Figure 4

The reaction of 1,2dichloro1,2diphenylethane with two equivalents of NaNH2 results in the formation of 1,2diphenylethyne. In this reaction, the strong base abstracts a proton from 1,2dichloro1,2diphenylethane to form the desired alkyne product.

Conclusion

The product that is formed by the reaction is 1,2diphenylethyne.

Interpretation Introduction

(d)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: A stepwise procedure of transforming an alkyne into a carbonyl group is known hydroboration-oxidation reaction. In a hydroboration-oxidation reaction, a terminal alkyne reacts with R2BH followed by H2O2, OH to form an aldehyde.

Expert Solution
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Answer to Problem 11.43P

The product that is formed by the reaction is heptanal.

Explanation of Solution

The reaction of hept1yne with R2BH followed by H2O2, OH is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  5

Figure 5

The reaction of hept1yne with R2BH followed by H2O2, OH results into the formation of alkenylborane of an aldehyde, heptanal. In this reaction, first of all, R2BH reacts with hept1yne to form an alkenylborane. Then, alkenylborane reacts with H2O2, OH to form hept1en1ol. Then, hept1en1ol undergoes tautomerization to form the desired product, heptanal.

Conclusion

The product that is formed by the reaction is heptanal.

Interpretation Introduction

(e)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

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Answer to Problem 11.43P

The product that is formed by the reaction is deuteroacetylene.

Explanation of Solution

The reaction of ethyn1ide with D2O is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  6

Figure 6

The reaction of ethyn1ide with D2O results in the formation of deuteroacetylene. In this reaction, the deuterium from D2O gets substituted to ethyn1ide that forms the desired alkyne product.

Conclusion

The product that is formed by the reaction is deuteroacetylene.

Interpretation Introduction

(f)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: A terminal alkyne reacts with H2O and H2SO4 (strong acid) to get hydrolyzed and forms an alcohol. In this case, hydrogen atom and OH will get attach to the less substituted carbon atom to form a stable carbocation.

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Answer to Problem 11.43P

The product that is formed by the reaction is (E)1cyclopentylprop1enol.

Explanation of Solution

The reaction of prop1yne1ylcyclopentane with H2O and H2SO4 (strong acid) is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  7

Figure 7

The reaction of prop1yne1ylcyclopentane with H2O and H2SO4 (strong acid) results in the formation of (E)1cyclopentylprop1enol. In this reaction, prop1yne1ylcyclopentane gets hydrolysed in the presence of strong acid that forms the desired product.

Conclusion

The product that is formed by the reaction is (E)1cyclopentylprop1enol.

Interpretation Introduction

(g)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

Expert Solution
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Answer to Problem 11.43P

The product that is formed by the reaction is hept3yne.

Explanation of Solution

The reaction of but1yne1ide with CH3CH2CH2OTs is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  8

Figure 8

The reaction of but1yne1ide with CH3CH2CH2OTs results in the formation of hept3yne. In this reaction, the alkyl group from CH3CH2CH2OTs gets substituted to but1yne1ide that forms the desired alkyne product.

Conclusion

The product that is formed by the reaction is hept3yne.

Interpretation Introduction

(h)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

Expert Solution
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Answer to Problem 11.43P

The product that is formed by the reaction is (1S,2R)2ethynyl1methylcyclohexanol.

Explanation of Solution

The reaction of (1S,6R)1methyl7oxacyclo[4.1.0]heptane with acetylide ion is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  9

Figure 9

The reaction of (1S,6R)1methyl7oxacyclo[4.1.0]heptane with acetylide ion results in the formation of (1S,2R)2ethynyl1methylcyclohexanol. In this reaction, epoxide ring gets open and the ethynyl group gets substituted to the intermediate that forms the desired alkyne product.

Conclusion

The product that is formed by the reaction is (1S,2R)2ethynyl1methylcyclohexanol.

Interpretation Introduction

(i)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

Expert Solution
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Answer to Problem 11.43P

The product that is formed by the reaction is pent2yne1ylcyclohexane.

Explanation of Solution

The reaction of but1yne with NaNH2 followed by other reagent is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  10

Figure 10

The reaction of but1yne with NaNH2 followed by (iodomethyl)cyclohexane results in the formation of pent2yne1ylcyclohexane. In this reaction, the strong base abstracts a proton from but1yne and cyclohexane ring gets substituted to the intermediate to form the desired alkyne product.

Conclusion

The product that is formed by the reaction is pent2yne1ylcyclohexane.

Interpretation Introduction

(j)

Interpretation: The product that is formed by the reaction is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The nucleophilic reaction that consists of bimolecular as well as bond-making and bond-breaking steps is termed as SN2 reactions. This is a one-step reaction in which both nucleophile and substrate participate in the rate determining step.

Expert Solution
Check Mark

Answer to Problem 11.43P

The product that is formed by the reaction is 4phenylbut3ynol.

Explanation of Solution

The reaction of ethynylbenzene with NaH followed by other reagent is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  11

Figure 11

The reaction of ethynylbenzene with NaH results in the formation of sodiumphenylethyn1ide. In this reaction, the strong base abstracts a proton from ethynyl that results in the formation of sodiumphenylethyn1ide.

The reaction of sodiumphenylethyn1ide with oxirane followed by water molecule is shown as,

Organic Chemistry, Chapter 11, Problem 11.43P , additional homework tip  12

Figure 12

The reaction of sodiumphenylethyn1ide with oxirane followed by water molecule results in the formation of 4phenylbut3ynol. In this reaction, sodiumphenylethyn1ide behaves as a nucleophile that opens the oxirane ring to the more substituted carbon that results in the formation of 4phenylbut3yn1olate. Then, 4phenylbut3yn1olate gets protonated by water molecule to form the desired product.

Conclusion

The product that is formed by the reaction is 4phenylbut3ynol.

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Chapter 11 Solutions

Organic Chemistry

Ch. 11 - Explain the following result. Although alkenes...Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.13PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.19PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.21PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.23PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.25PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - Prob. 11.27PCh. 11 - Give the IUPAC name for each alkyne.Ch. 11 - Prob. 11.29PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.31PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - Draw the products formed when 3-hexyne is treated...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - What alkynes give each of the following ketones as...Ch. 11 - Prob. 11.41PCh. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - Prob. 11.43PCh. 11 - Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.45PCh. 11 - Prob. 11.46PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.52PCh. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - Prob. 11.55PCh. 11 - Synthesize each compound from acetylene. You may...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.61PCh. 11 - Prob. 11.62PCh. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.65PCh. 11 - Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.67PCh. 11 - 11.65 Explain why an optically active solution of ...
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