ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 11, Problem 11.33P

Draw the products formed when hex 1 yne is treated with each reagent.

a. HCl ( 2 equiv )

b. HBr ( 2 equiv )

c. Cl 2 ( 2 equiv )

d. H 2 O + H 2 SO 4 + HgSO 4

e. [ 1 ] R 2 BH; [ 2 ] H 2 O 2 , HO

f. NaH

g. [ 1 ] NH 2 ; [ 2 ] CH 3 CH 2 Br

h. [ 1 ] NH 2 ; [2] Chapter 11, Problem 11.33P, 11.33   Draw the products formed when  is treated with each reagent.







[2] ;
 ; [ 3 ] H 2 O

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The product that is formed by the reaction of hex1yne with HCl(2equiv) 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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with HCl(2equiv) is 2,2dichlorohexane.

Explanation of Solution

The reaction of hex1yne with HCl(2equiv) is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  1

Figure 1

The reaction of hex1yne with HCl(2equiv) results in the formation of 2,2dichlorohexane. In this reaction, the negatively charged chloride ion from two equivalents of HCl gets substituted on the highly substituted carbon atom of hex1yne to form the desired dihalide product.

Conclusion

The product that is formed by the reaction of hex1yne with HCl(2equiv) is 2,2dichlorohexane.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The product that is formed by the reaction of hex1yne with HBr(2equiv) 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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with HBr(2equiv) is 2,2dibromohexane.

Explanation of Solution

The reaction of hex1yne with HBr(2equiv) is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  2

Figure 2

The reaction of hex1yne with HBr(2equiv) results in the formation of 2,2dibromohexane. In this reaction, the negatively charged bromide ion from two equivalents of HBr gets substituted on the highly substituted carbon atom of hex1yne to form the desired dihalide product.

Conclusion

The product that is formed by the reaction of hex1yne with HBr(2equiv) is 2,2dibromohexane.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The product that is formed by the reaction of hex1yne with Cl2(2equiv) 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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with Cl2(2equiv) is 1,1,2,2tetrachlorohexane.

Explanation of Solution

The reaction of hex1yne with Cl2(2equiv) is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  3

Figure 3

The reaction of hex1yne with Cl2(2equiv) results in the formation of 1,1,2,2tetrachlorohexane. In this reaction, the negatively charged chloride ion from two equivalents of Cl2 gets substituted on the highly substituted carbon atom of hex1yne to form the desired tetrahalide product.

Conclusion

The product that is formed by the reaction of hex1yne with Cl2(2equiv) is 1,1,2,2tetrachlorohexane.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The product that is formed by the reaction of hex1yne with H2O+H2SO4+HgSO4 is to be drawn.

Concept introduction: A terminal alkyne reacts with H2O, H2SO4 (strong acid) and HgSO4 to form a ketone. In this case, hydrogen atom and OH will get attach to the less substituted carbon atom to form a stable carbocation.

The chemical equilibrium that exists between a keto form of a compound and an enol form of the same compound is known as keto-enol tautomerism. Tautomers refer to these keto and enol forms.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with H2O+H2SO4+HgSO4 is hexan2one.

Explanation of Solution

The reaction of hex1yne with H2O+H2SO4+HgSO4 is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  4

Figure 4

The reaction of hex1yne with H2O+H2SO4+HgSO4 results in the formation of hex1ene2ol. The terminal alkyne, hex1yne reacts with the reagents H2O, HgSO4 in the presence of strong acid H2SO4 to form hex1ene2ol as the desired product.

Then, the enol form, hex1ene2ol forms a keto form that is shown below.

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  5

Figure 5

Thus, the keto-enol tautomerization of hex1ene2ol forms the desired product, hexan2one.

Conclusion

The product that is formed by the reaction of hex1yne with H2O+H2SO4+HgSO4 is hexan2one.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The product that is formed by the reaction of hex1yne with [1]R2BH;[2]H2O2,HO 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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with [1]R2BH;[2]H2O2,HO is hexanal.

Explanation of Solution

The reaction of hex1yne [1]R2BH is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  6

Figure 6

The reaction of hex1yne with [1]R2BH results into the formation of alkenylborane.

Then, the reaction of alkenylborane with [2]H2O2,HO is shown below.

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  7

Figure 7

Thus, the reaction of alkenylborane with [2]H2O2,HO results in the formation of hex1en1ol.

In the last step, hex1en1ol undergoes tautomerization as shown below.

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  8

Figure 8

Thus, the tautomerization of hex1en1ol forms the desired product, hexanal.

Conclusion

The product that is formed by the reaction of hex1yne with [1]R2BH;[2]H2O2,HO is hexanal.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The product that is formed by the reaction of hex1yne with NaH 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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with NaH is hex1yn1ide.

Explanation of Solution

The reaction of hex1yne with NaH is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  9

Figure 9

The reaction of hex1yne with NaH results in the formation of hex1yn1ide. In this reaction, the strong base abstracts a proton from hex1yne to form the desired anionic product.

Conclusion

(a) The product that is formed by the reaction of hex1yne with NaH is hex1yn1ide.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The product that is formed by the reaction of hex1yne with [1]NH2;[2]CH3CH2Br 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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with [1]NH2;[2]CH3CH2Br is oct3yne.

Explanation of Solution

The reaction of hex1yne with [1]NH2 is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  10

Figure 10

The reaction of hex1yne with [1]NH2 results in the formation of hex1yn1ide. In this reaction, the strong base abstracts a proton from hex1yne to form the anionic compound.

Then, the reaction of hex1yn1ide with ethyl bromide is shown below.

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  11

Figure 11

Thus, in the above reaction, hex1yn1ide behaves as a nucleophile that attach to the ethyl group and forms the desired product, oct3yne.

Conclusion

The product that is formed by the reaction of hex1yne with [1]NH2;[2]CH3CH2Br is oct3yne.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The product that is formed by the reaction of hex1yne with [1]NH2;ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  12;[3]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.

Answer to Problem 11.33P

The product that is formed by the reaction of hex1yne with [1]NH2;ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  13;[3]H2O is oct3yne1ol.

Explanation of Solution

The reaction of hex1yne with [1]NH2 is shown as,

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  14

Figure 12

The reaction of hex1yne with [1]NH2 results in the formation of hex1yn1ide. In this reaction, the strong base abstracts a proton from hex1yne to form the anionic compound.

Then, the reaction of hex1yn1ide with oxirane is shown below.

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  15

Figure 13

Thus, in the above reaction, hex1yn1ide behaves as a nucleophile that opens the oxirane ring to the more substituted carbon that results in the formation of oct3yn1olate.

Then, the reaction of oct3yn1olate with water molecule is shown below.

ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  16

Figure 14

Thus, in the above reaction, oct3yn1olate gets protonated to form the desired alcoholic product, oct3yne1ol.

Conclusion

The product that is formed by the reaction of hex1yne with [1]NH2;ORGANIC CHEMISTRY, Chapter 11, Problem 11.33P , additional homework tip  17;[3]H2O is oct3yne1ol.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Draw the products formed in each reaction.
Draw the products of each reaction.
What is the correct reagent?

Chapter 11 Solutions

ORGANIC CHEMISTRY

Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.12PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.14PCh. 11 - Problem 11.15 Draw the organic products formed in...Ch. 11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.18PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.20PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.22PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.24PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne. a. ...Ch. 11 - Prob. 11.27PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.29PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - Prob. 11.35PCh. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.39 Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - 11.46 Tautomerization in base resembles...Ch. 11 - 11.47 Draw a stepwise mechanism for each...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.51 Synthesize each compound from acetylene. You...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.62PCh. 11 - 11.63 Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.64PCh. 11 - 11.65 Explain why an optically active solution of ...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License