ORGANIC CHEMISTRY-PRINT COMPANION (LL)
ORGANIC CHEMISTRY-PRINT COMPANION (LL)
3rd Edition
ISBN: 9781119444251
Author: Klein
Publisher: WILEY
Question
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Chapter 25, Problem 40PP

(a)

Interpretation Introduction

Interpretation:

Bond-line structure for the given set of amino acids in zwitterionic form need to be drawn.

Concept introduction:

Bond-line structure is the representation of organic structural formulas in a shorthand manner.  In this case only the bond between carbon and other atoms are shown except hydrogen.  It is understood that all the remaining valency to be filled by hydrogen.  Apart from carbon atoms the other atoms are shown along with hydrogen.

Zwitterion is the one which has the positively and negatively charged groups separately.  Zwitterion is found at the pH which is the isoelectric point.

To draw : To draw bond-line structure for L-valine

(a)

Expert Solution
Check Mark

Answer to Problem 40PP

The bond-line structure for (a) and its zwitterion form is

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  1

Explanation of Solution

Linear formula for L-valine

The linear formula for L-valine is (CH3)2CHCH(NH2)CO2H .

Draw bonds between the atoms except hydrogen

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  2

The structure from the linear formula is drawn as shown above.  Considering the valency of carbon to be four, the structure is drawn.

Remove the carbons that are explicitly shown

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  3

The carbon atoms are ignored from being explicitly shown as it is understood that the carbon and hydrogen atoms are not shown in bond-line structure.

Assign configuration

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  4

As in the name of the problem statement it is said L-valine, the chiral center must have “S” configuration and the same is shown in the above structure.

Zwitterion

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  5

Zwitterion is one of the form in which the charge is separated and this is formed at a particular pH known as isoelectric point.

(b)

Interpretation Introduction

Interpretation:

Bond-line structure for the given set of amino acids in zwitterionic form need to be drawn.

Concept introduction:

Bond-line structure is the representation of organic structural formulas in a shorthand manner.  In this case only the bond between carbon and other atoms are shown except hydrogen.  It is understood that all the remaining valency to be filled by hydrogen.  Apart from carbon atoms the other atoms are shown along with hydrogen.

Zwitterion is the one which has the positively and negatively charged groups separately.  Zwitterion is found at the pH which is the isoelectric point.

To draw : To draw bond-line structure for L-tryptophan

(b)

Expert Solution
Check Mark

Answer to Problem 40PP

The bond-line structure for (b) and its zwitterion form is

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  6

Explanation of Solution

Linear formula for L-tryptophan

The linear formula for L-tryptophan is (C8H6N)CH2CH(NH2)CO2H .

Draw bonds between the atoms except hydrogen

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  7

The structure from the linear formula is drawn as shown above.  Considering the valency of carbon to be four, the structure is drawn.  The benzopyroole ring is the one which is represented as C8H6N in the linear formula.

Remove the carbons that are explicitly shown

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  8

The carbon atoms are ignored from being explicitly shown as it is understood that the carbon and hydrogen atoms are not shown in bond-line structure.

Assign configuration

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  9

As in the name of the problem statement it is said L-tryptophan, the chiral center must have “S” configuration and the same is shown in the above structure.

Zwitterion

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  10

Zwitterion is one of the form in which the charge is separated and this is formed at a particular pH known as isoelectric point.

(c)

Interpretation Introduction

Interpretation:

Bond-line structure for the given set of amino acids in zwitterionic form need to be drawn.

Concept introduction:

Bond-line structure is the representation of organic structural formulas in a shorthand manner.  In this case only the bond between carbon and other atoms are shown except hydrogen.  It is understood that all the remaining valency to be filled by hydrogen.  Apart from carbon atoms the other atoms are shown along with hydrogen.

Zwitterion is the one which has the positively and negatively charged groups separately.  Zwitterion is found at the pH which is the isoelectric point.

To draw : To draw bond-line structure for L-glutamine

(c)

Expert Solution
Check Mark

Answer to Problem 40PP

The bond-line structure for (c) and its zwitterion form is

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  11

Explanation of Solution

Linear formula for L-glutamine

The linear formula for L-glutamine is H2NCOCH2CH2CH(NH2)CO2H .

Draw bonds between the atoms except hydrogen

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  12

The structure from the linear formula is drawn as shown above.  Considering the valency of carbon to be four, the structure is drawn.

Remove the carbons that are explicitly shown

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  13

The carbon atoms are ignored from being explicitly shown as it is understood that the carbon and hydrogen atoms are not shown in bond-line structure.

Assign configuration

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  14

As in the name of the problem statement it is said L-glutamine, the chiral center must have “S” configuration and the same is shown in the above structure.

Zwitterion

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  15

Zwitterion is one of the form in which the charge is separated and this is formed at a particular pH known as isoelectric point.

(d)

Interpretation Introduction

Interpretation:

Bond-line structure for the given set of amino acids in zwitterionic form need to be drawn.

Concept introduction:

Bond-line structure is the representation of organic structural formulas in a shorthand manner.  In this case only the bond between carbon and other atoms are shown except hydrogen.  It is understood that all the remaining valency to be filled by hydrogen.  Apart from carbon atoms the other atoms are shown along with hydrogen.

Zwitterion is the one which has the positively and negatively charged groups separately.  Zwitterion is found at the pH which is the isoelectric point.

To draw : To draw bond-line structure for L-proline

(d)

Expert Solution
Check Mark

Answer to Problem 40PP

The bond-line structure for (d) and its zwitterion form is

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  16

Explanation of Solution

Draw bonds between the atoms except hydrogen

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  17

The structure from the linear formula is drawn as shown above.  Considering the valency of carbon to be four, the structure is drawn.

Remove the carbons that are explicitly shown

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  18

The carbon atoms are ignored from being explicitly shown as it is understood that the carbon and hydrogen atoms are not shown in bond-line structure.

Assign configuration

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  19

As in the name of the problem statement it is said L-proline, the chiral center must have “S” configuration and the same is shown in the above structure.

Zwitterion

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 25, Problem 40PP , additional homework tip  20

Zwitterion is one of the form in which the charge is separated and this is formed at a particular pH known as isoelectric point.

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Chapter 25 Solutions

ORGANIC CHEMISTRY-PRINT COMPANION (LL)

Ch. 25.2 - Prob. 10CCCh. 25.3 - Prob. 11CCCh. 25.3 - Prob. 12CCCh. 25.3 - Prob. 13CCCh. 25.3 - Prob. 2LTSCh. 25.3 - Prob. 14PTSCh. 25.3 - Prob. 15ATSCh. 25.3 - Prob. 16ATSCh. 25.3 - Prob. 17CCCh. 25.3 - Prob. 18CCCh. 25.3 - Prob. 19CCCh. 25.3 - Prob. 20CCCh. 25.4 - Prob. 3LTSCh. 25.4 - Prob. 21PTSCh. 25.4 - Prob. 22ATSCh. 25.4 - Prob. 23ATSCh. 25.4 - Prob. 24ATSCh. 25.4 - Prob. 25CCCh. 25.4 - Prob. 26CCCh. 25.4 - Prob. 27CCCh. 25.4 - Prob. 28CCCh. 25.4 - Prob. 29CCCh. 25.5 - Prob. 30CCCh. 25.5 - Prob. 4LTSCh. 25.5 - Prob. 31PTSCh. 25.5 - Prob. 32ATSCh. 25.5 - Prob. 33ATSCh. 25.6 - Prob. 5LTSCh. 25.6 - Prob. 34PTSCh. 25.6 - Prob. 35ATSCh. 25.6 - Prob. 36ATSCh. 25.6 - Prob. 6LTSCh. 25.6 - Prob. 37PTSCh. 25.6 - Prob. 38ATSCh. 25.7 - Prob. 39CCCh. 25 - Prob. 40PPCh. 25 - Prob. 41PPCh. 25 - Prob. 42PPCh. 25 - Prob. 43PPCh. 25 - Prob. 44PPCh. 25 - Prob. 45PPCh. 25 - Prob. 46PPCh. 25 - Prob. 47PPCh. 25 - Prob. 48PPCh. 25 - Prob. 49PPCh. 25 - Prob. 50PPCh. 25 - Prob. 51PPCh. 25 - Prob. 52PPCh. 25 - Prob. 53PPCh. 25 - Prob. 54PPCh. 25 - Prob. 55PPCh. 25 - Prob. 56PPCh. 25 - Prob. 57PPCh. 25 - Prob. 58PPCh. 25 - Prob. 59PPCh. 25 - Prob. 60PPCh. 25 - Prob. 61PPCh. 25 - Prob. 62PPCh. 25 - Prob. 63PPCh. 25 - Prob. 64PPCh. 25 - Prob. 65PPCh. 25 - Prob. 66PPCh. 25 - Prob. 67PPCh. 25 - Prob. 68PPCh. 25 - Prob. 69PPCh. 25 - Prob. 70PPCh. 25 - Prob. 71PPCh. 25 - Prob. 72PPCh. 25 - Prob. 73PPCh. 25 - Prob. 74PPCh. 25 - Prob. 75PPCh. 25 - Prob. 76PPCh. 25 - Prob. 77PPCh. 25 - Prob. 78PPCh. 25 - Prob. 79PPCh. 25 - Prob. 80PPCh. 25 - Prob. 81PPCh. 25 - Prob. 82PPCh. 25 - Prob. 83PPCh. 25 - Prob. 84IPCh. 25 - Prob. 85IPCh. 25 - Prob. 86IPCh. 25 - Prob. 87IPCh. 25 - Prob. 88IPCh. 25 - Prob. 89IPCh. 25 - Prob. 90CPCh. 25 - We saw in Section 25.6 that DCC can be used to...Ch. 25 - Prob. 92CP
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