Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
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Chapter 13, Problem 13.28P
Interpretation Introduction

(a)

Interpretation:

The given synthesis scheme is to be converted to word form that can be used as instructions in the laboratory.

Concept introduction:

The synthesis scheme is the balanced chemical equation written for carrying out a sequence of reactions with specified steps. The synthetic step displays that the reactants are converted to the product by reacting with reagents in the required conditions.

The structures on the left side of the reaction arrow (Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  1) are the reactants. The reagents used are written above the arrow, and the reaction conditions including solvent, temperature, pH, time of reaction, etc. are written below the arrow. If more than one sequence is combined in one step, then the reagents are numbered according to their sequence and can be written above and below the reaction arrow. In such cases, the reaction conditions are separated from the reactant or reagent by either a comma or a slash. The numbers given to reagents represent that the reaction goes to completion before the next reagent is added. The structures on the right side of the reaction arrow

(Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  2) are the products. The product of the previous step is the reactant of the next step. While writing the synthetic scheme in word form, the functional groups involved in the reactants and the functional groups produced in the product are to be identified.

Expert Solution
Check Mark

Answer to Problem 13.28P

The word form for the given synthesis scheme is:

The starting epoxide reacts with phenylmagnesium bromide in the solvent diethyl ether followed by aqueous acid, to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  3. Then, treat Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  4 with phosphoric acid at Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  5to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  6.

Explanation of Solution

The given synthesis scheme is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  7

In the given synthetic route, the reactant having functional group epoxide is converted to an alcohol named Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  8 which is further converted to an alkene named Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  9 on reaction with appropriate reagents as mentioned. In the first step, the first reagent used is phenylmagnesium bromide in the solvent diethyl ether, and the second reagent is Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  10 which represents the aqueous acidic condition. In the second step, the reagent is phosphoric acid and Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  11 is the reaction temperature. Thus, the word form of the above synthetic scheme can be written as follows:

The starting epoxide reacts with phenylmagnesium bromide in the solvent diethyl ether followed by aqueous acid, to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  12. Then, treat Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  13 with phosphoric acid at Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  14to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  15.

Conclusion

The given synthesis scheme is converted to word form by identifying the names of reactants, reagents, and products.

Interpretation Introduction

(b)

Interpretation:

The given synthesis scheme is to be converted to word form that can be used as instructions in the laboratory.

Concept introduction:

The synthesis scheme is the balanced chemical equation written for carrying out a sequence of reactions with specified steps. The synthetic step displays that the reactants are converted to products by reacting with the reagents in the required conditions.

The structures on the left side of the reaction arrow (Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  16) are the reactants. The reagents used are written above the arrow, and the reaction conditions including solvent, temperature, pH, time of reaction, etc. are written below the arrow. If more than one sequence is combined in one step, then the reagents are numbered according to their sequence and can be written above and below the reaction arrow. In such cases, the reaction conditions are separated from the reactant or reagent by either a comma or a slash. The numbers given to reagents represent that the reaction goes to completion before the next reagent is added. The structures on right side of the reaction arrow (Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  17) are the products. The product of the previous step is the reactant of the next step. While writing the synthetic scheme in word form, the functional groups involved in the reactants and the functional groups produced in the product are to be identified.

Expert Solution
Check Mark

Answer to Problem 13.28P

The word form for the given synthesis scheme is:

Phenylehtanone reacts with lithium diisopropylamide followed by iodomethane, to produce phenylpropanone. Then, add the molecular bromine in the presence of acetic acid to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  18which further reacts with sodium acetate to yield the final product.

Explanation of Solution

The given synthesis scheme is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  19

The given synthetic route is of three steps. In the first step, the reactant having functional group ketone named phenylehtanone is converted to another ketone named phenylpropanone. In the second step, phenylpropanone is converted to Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  20alpha bromo ketone named Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  21, which, in the third step, is further converted to the final product having the ester functional group. In the first step, the first reagent used is lithium diisopropylamide, and the second reagent is iodomethane. In the second step, the reagent is molecular bromine in acetic acid. The reagent for the third step is sodium acetate. Thus, the word form of the above synthetic scheme can be written as follows:

Phenylehtanone reacts with lithium diisopropylamide followed by iodomethane to produce phenylpropanone. Add the molecular bromine in presence of acetic acid to phenylpropanone to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  22which further reacts with sodium acetate to yield THE final product.

Conclusion

The given synthesis scheme was converted to word form by identifying the names of reactants, reagents, and products.

Interpretation Introduction

(c)

Interpretation:

The given synthesis scheme is to be converted to word form that can be used as instructions in the laboratory.

Concept introduction:

The synthesis scheme is the balanced chemical equation written for carrying out a sequence of reactions with specified steps. The synthetic step displays that the reactants are converted to the product by reacting with reagents in the required conditions.

The structures on the left side of the reaction arrow (Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  23) are the reactants. The reagents used are written above the arrow, and the reaction conditions including solvent, temperature, pH, time of reaction, etc. are written below the arrow. If more than one sequence is combined in one step, then the reagents are numbered according to their sequence and can be written above and below the reaction arrow. In such cases, the reaction conditions are separated from the reactant or reagent by either a comma or a slash. The numbers given to reagents represent that the reaction goes to completion before the next reagent is added. The structures on right side of the reaction arrow (Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  24) are the products. The product of the previous step is the reactant of the next step. While writing the synthetic scheme in word form, the functional groups involved in the reactants, and the functional groups produced in the product are to be identified.

Expert Solution
Check Mark

Answer to Problem 13.28P

The word form for the given synthesis scheme is:

Heat Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  25 in aqueous hydrochloric acid to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  26, add phosphorous tribromide to it to produce Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  27. Then, react Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  28 with sodium azide to yield the final product.

Explanation of Solution

The given synthesis scheme is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  29

The given synthetic route is of three steps. The nitro functional group remains as it is throughout the reaction sequence, and so, is not considered. In the first step, ether functional group is converted to an alcohol. In the second step, Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  30 group of alcohol is replaced by bromine, which in the third step is replaced by Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  31. In the first step, the reagent used is Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  32 that represents acidic condition where Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  33 is the symbol used for heat. In the second step, the reagent is Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  34, phosphorous tribromide, and in the third step, the reagent used is sodium azide, Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  35. Thus, the word form of the above synthetic scheme can be written as follows:

Heat Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  36 in aqueous hydrochloric acid to form Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  37, and add phosphorous tribromide to it to produce Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  38. Then, react Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 13, Problem 13.28P , additional homework tip  39 with sodium azide to yield the final product.

Conclusion

The given synthesis scheme was converted to word form by identifying the names of reactants, reagents, and products.

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