Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 11, Problem 11.21P
Interpretation Introduction

(a)

Interpretation: The product that is formed by the reaction of CH3CH2CCNa+ with CH3CH2CH2Br 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 11.21P

The product that is formed by the reaction of CH3CH2CCNa+ with CH3CH2CH2Br is,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  1

Explanation of Solution

The reaction of CH3CH2CCNa+ with CH3CH2CH2Br is shown as,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  2

Figure 1

Thus, the product that is formed by the reaction of but1yn1ylsodium, CH3CH2CCNa+ with propyl bromide, CH3CH2CH2Br is hept3yne. In the above reaction, butylate anion behaves as a strong nucleophile which undergoes nucleophilic substitution reaction with propyl bromide or 1bromopropane (primary alkyl halide). Thus, in this reaction, NaBr gets eliminated that result in the formation of the desired product, hept3yne.

Conclusion

The product that is formed by the reaction of CH3CH2CCNa+ with CH3CH2CH2Br is hept3yne.

Interpretation Introduction

(b)

Interpretation: The product that is formed by the reaction of CH3CH2CCNa+ with (CH3)2CHCH2CH2Cl 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 11.21P

The product that is formed by the reaction of CH3CH2CCNa+ with (CH3)2CHCH2CH2Cl is,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  3

Explanation of Solution

The reaction of CH3CH2CCNa+ with (CH3)2CHCH2CH2Cl is shown as,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  4

Figure 2

Thus, the product that is formed by the reaction of but1yn1ylsodium, CH3CH2CCNa+ with 1chloro3methylbutane, (CH3)2CHCH2CH2Cl is 7methyloct3yne. In the above reaction, butylate anion behaves as a strong nucleophile which undergoes nucleophilic substitution reaction with 1chloro3methylbutane (primary alkyl halide). Thus, in this reaction, NaCl gets eliminated that result in the formation of the desired product, 7methyloct3yne.

Conclusion

The product that is formed by the reaction of CH3CH2CCNa+ with (CH3)2CHCH2CH2Cl is 7methyloct3yne.

Interpretation Introduction

(c)

Interpretation: The product that is formed by the reaction of CH3CH2CCNa+ with (CH3CH2)3CCl is to be drawn.

Concept introduction: The bimolecular elimination reaction that favours the removal of a HX substituent from an alkyl halide that needs a base to remove H from carbon adjacent to the leaving group that in turn forms a double bond is termed E2 elimination reaction.

Expert Solution
Check Mark

Answer to Problem 11.21P

The product that is formed by the reaction of CH3CH2CCNa+ with (CH3CH2)3CCl is,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  5

Explanation of Solution

The reaction of CH3CH2CCNa+ with (CH3CH2)3CCl is shown as,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  6

Figure 3

Thus, the products that are formed by the reaction of but1yn1ylsodium, CH3CH2CCNa+ with 3chloro3ethylpentane, (CH3CH2)3CCl are 3ethylpent2ene and but1yne. Butylate anion behaves as a strong nucleophile, but in case of secondary and tertiary alkyl halide, it undergoes E2 elimination reaction due to steric hindrance. Thus, the butylate anion undergoes E2 elimination reaction with 3chloro3ethylpentane (tertiary alkyl halide). Thus, this results in the formation of two products, 3ethylpent2ene and but1yne.

Conclusion

The products that are formed by the reaction of CH3CH2CCNa+ with (CH3CH2)3CCl are 3ethylpent2ene and but1yne.

Interpretation Introduction

(d)

Interpretation: The product that is formed by the reaction of CH3CH2CCNa+ with BrCH2CH2CH2CH2OH 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 11.21P

The product that is formed by the reaction of CH3CH2CCNa+ with BrCH2CH2CH2CH2OH is,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  7

Explanation of Solution

The reaction of CH3CH2CCNa+ with BrCH2CH2CH2CH2OH is shown as,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  8

Figure 4

Thus, the major product that is formed by the reaction of but1yn1ylsodium, CH3CH2CCNa+ with 4bromobutan1ol, BrCH2CH2CH2CH2OH is but1yne. In this reaction, butylate anion behaves as a strong nucleophile. Thus, it abstracts an acidic hydrogen atom from the alcoholic group.. Thus, this results in the formation of two products, 4bromobutan1olate (minor) and but1yne (major).

Conclusion

The major product that is formed by the reaction of CH3CH2CCNa+ with BrCH2CH2CH2CH2OH is but1yne.

Interpretation Introduction

(e)

Interpretation: The product that is formed by the reaction of CH3CH2CCNa+ with ethylene oxide followed by H2O 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 11.21P

The product that is formed by the reaction of CH3CH2CCNa+ with ethylene oxide followed by H2O is,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  9

Explanation of Solution

The reaction of CH3CH2CCNa+ with ethylene oxide or oxirane followed by H2O is shown as,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  10

Figure 5

Thus, the major product that is formed by the reaction of but1yn1ylsodium, CH3CH2CCNa+ with ethylene oxide or oxirane followed by H2O is hex3yne1ol. In this reaction, butylate anion behaves as a strong nucleophile which on reaction with oxirane forms hex3yne1ol.

Conclusion

The product that is formed by the reaction of CH3CH2CCNa+ with ethylene oxide followed by H2O is hex3yne1ol.

Interpretation Introduction

(f)

Interpretation: The product that is formed by the reaction of CH3CH2CCNa+ with propene oxide followed by H2O 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 11.21P

The product that is formed by the reaction of CH3CH2CCNa+ with propene oxide followed by H2O is,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  11

Explanation of Solution

The reaction of CH3CH2CCNa+ with propene oxide or 2methyloxirane followed by H2O is shown as,

Organic Chemistry-Package(Custom), Chapter 11, Problem 11.21P , additional homework tip  12

Figure 6

Thus, the major product that is formed by the reaction of but1yn1ylsodium, CH3CH2CCNa+ with propene oxide or 2methyloxirane followed by H2O is hept4yne2ol. In this reaction, butylate anion behaves as a strong nucleophile which on reaction with 2methyloxirane forms hept4yne2ol.

Conclusion

The product that is formed by the reaction of CH3CH2CCNa+ with propene oxide followed by H2O is hept4yne2ol.

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Chapter 11 Solutions

Organic Chemistry-Package(Custom)

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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