Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
bartleby

Concept explainers

Question
Book Icon
Chapter 17, Problem 17.22AP
Interpretation Introduction

(a)

Interpretation:

The principal organic compound that is expected when trans-2-butene is reacted with Br2 in CH2Cl2, dark is to be stated.

Concept introduction:

The addition reaction of the alkene are very well known reactions. The electron density on the alkene double bond makes it nucleophilic. The alkene undergoes varieties of addition reaction via different mechanisms.

Expert Solution
Check Mark

Answer to Problem 17.22AP

The principal organic compound that is formed when trans-2-butene is reacted with Br2 in CH2Cl2, dark is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  1

Explanation of Solution

The reaction of trans-2-butene when reacted with Br2 in CH2Cl2, dark is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  2

Figure 1

The addition of the bromine molecule on the double bond of the alkene takes place to give the dibromo product. The addition of bromine to the double bond is the anti-addition.

Conclusion

The principal organic compound that is formed when trans-2-butene is reacted with Br2 in CH2Cl2, dark is shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The principal organic compound that is expected when trans-2-butene is reacted N-bromosuccinimide in CCl4, light is to be stated.

Concept introduction:

The addition reactions of the alkene are very well known reactions. The electron density on the alkene double bond makes it nucleophilic. The alkene undergoes varieties of addition reaction via different mechanisms.

Expert Solution
Check Mark

Answer to Problem 17.22AP

The principal organic compound that is formed when trans-2-butene is reacted with N-bromosuccinimide in CCl4, light is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  3

Explanation of Solution

The reaction of trans-2-butene when reacted with N-bromosuccinimide in CCl4, light is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  4

Figure 2

The reaction of an alkene with N-bromosuccinimide in the presence is the free-radical reaction. In this reaction, allylic bromination is observed instead of an addition to the alkene. The N-bromosuccinimide acts as radical initiator. This molecule breaks the NBr bond homolytically to give bromine radical. The bromine takes up the allylic hydrogen and leads to the formation of the allylic carbocation. The allylic carbocation is resonance stabilized and leads to the formation of two resonating structures. These two resonating structures than reacts with bromine molecule produced in the reaction to give the allylic brominated products for both resonating structures.

Conclusion

The principal organic compound that is formed when trans-2-butene is reacted with N-bromosuccinimide in CCl4, light is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The principal organic compound that is expected when product(s) of part (b) undergo solvolysis in aqueous acetone is to be stated.

Concept introduction:

The nucleophilic substitution reactions are the reactions in which a group is substituted by a nucleophile. The rate of reaction depends upon the nucleophilicity and concentration of the nucleophile.

The SN2 reaction is a nucleophilic substitution bimolecular reaction in which the addition of nucleophile and elimination of a leaving group takes place simultaneously. The rate of reaction depends upon both the substrate and reactant in the rate law equation.

Expert Solution
Check Mark

Answer to Problem 17.22AP

The principal organic compounds that are formed when product(s) of part (b) undergo solvolysis in aqueous acetone are shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  5

Explanation of Solution

The products of part (b) are shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  6

Figure 3

The reaction when product(s) of part (b) undergo solvolysis in aqueous acetone is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  7

Figure 4

The nucleophilic substitution reaction takes place when solvolysis of products of part (b) takes place. The bromine group is substituted by the hydroxyl group giving rise to the formation of an allylic alcohol.

Conclusion

The principal organic compound that is formed when product(s) of part (b) undergo solvolysis in aqueous acetone is shown in Figure 4.

Interpretation Introduction

(d)

Interpretation:

The principal organic compound that is expected when product(s) of part (b) are reacted with Mg in ether is to be stated.

Concept introduction:

The reaction of an alkyl halide with a metal-like magnesium in the presence of dry ether leads to the formation of RMgX (organometallic compounds) also known as a Grignard reagent. These compounds are very sensitive to moisture or polar hydrogens reacts immediately leading to the formation of alkane of the alkyl group.

Expert Solution
Check Mark

Answer to Problem 17.22AP

The principal organic compounds that are formed when product(s) of part (b) are reacted with Mg in ether is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  8

Explanation of Solution

The products of part (b) are shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  9

Figure 3

The reaction that occurs when product(s) of part (b) are reacted with Mg in ether is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  10

Figure 5

The allylic halide also undergoes the same kind of reactions are do the alkyl halide with magnesium metal in dry ether. They are also lead to the formation of Grignard reagent but this time with the allylic group.

Conclusion

The principal organic compound that is formed when product(s) of part (b) undergo solvolysis in aqueous acetone is shown in Figure 5.

Interpretation Introduction

(e)

Interpretation:

The principal organic compound that is expected when product(s) of part (d) are reacted with D2O is to be stated.

Concept introduction:

The reaction of an alkyl halide with a metal-like magnesium in the presence of dry ether leads to the formation of RMgX (organometallic compounds) also known as a Grignard reagent. These compounds are very sensitive to moisture or polar hydrogens reacts immediately leading to the formation of alkane of the alkyl group.

Expert Solution
Check Mark

Answer to Problem 17.22AP

The principal organic compound that is formed when products of part (d) react with D2O is shown shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  11

Explanation of Solution

The products of part (d) are shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  12

Figure 6

The Gringnard reagents react with D2O to from deuterated alkenes. The MgBr groups are get replaced by D. The corresponding chemical reaction is shown below.

Organic Chemistry, Chapter 17, Problem 17.22AP , additional homework tip  13

Figure 7

Conclusion

The principal organic compound that is formed when products of part (d) react with D2O is shown in Figure 7.

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
3. Outline a synthetic scheme for the preparation of the compounds A from the suggested starting material by the suggested method. Make sure to clearly indicate all reagents needed to perform each step of the synthetic scheme. (a) OH O=S=O Br A (b) H₂N. (c) HO3S. Br Br A A 1 Br
Predict the products of reaction of pent-1-yne with the following reagents.(a) 1 equivalent of HCl (b) 2 equivalents of HCl (c) excess H2, Ni(d) H2, Pd>BaSO4, quinoline
Suggest readily available starting materials and reaction conditions suitable for obtaining each of the following compounds by a procedure involving alkylation of nucleophilic carbon. (a) PHCH2CH2CHPH (b) (CH3)½C=CHCH2CH2CCH2CO;CH3 ČN (c) (d) CH2=CHCH=CHCH2CH2CO,H CH3 CH2CO2H CH3 CH3CO CH;CH2CH2 (f) (e) 2,3-diphenylpropanoic acid (g) CH3Oʻ CH3CH2 CH2CH=CH2
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.
Similar questions
SEE MORE QUESTIONS
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