Chapter 29, Problem 29.40P

Draw the organic product formed when the amino acid leucine is treated with each reagent.

a. ${\text{CH}}_{\text{3}}\text{OH,}{\text{H}}^{+}$ g. ${\text{C}}_6{\text{H}}_5\text{COCl}$, pyridine

b. ${\text{CH}}_{\text{3}}\text{COCl}$, pyridine h. ${\left[{\left({\text{CH}}_{\text{3}}\right)}_3\text{COCO}\right]}_2\text{O,}{\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_3\text{N}$

c. ${\text{C}}_6{\text{H}}_5{\text{CH}}_2\text{OH,}{\text{H}}^{+}$ i. The product in (d), then ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}+\text{DCC}$

d. ${\text{Ac}}_{\text{2}}\text{O}$, pyridine j. The product in (h), then ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}+\text{DCC}$

e. $\text{HCl}\left(\text{1}\text{equiv}\right)$ k. $\text{Fmoc}-\text{Cl,}{\text{Na}}_{\text{2}}{\text{CO}}_{\text{3}},{\text{H}}_{\text{2}}\text{O}$

f. $\text{NaOH}\left(1\text{equiv}\right)$ l. ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{N}=\text{C}=\text{S}$

Interpretation Introduction

(a)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{CH}}_{\text{3}}\text{OH,}{\text{H}}^{+}$.

The reaction between leucine and ${\text{CH}}_{\text{3}}\text{OH,}{\text{H}}^{+}$ involves protection of carbonyl group by as an ester. The corresponding reaction is shown below.

Figure 1

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 2

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 2.

Interpretation Introduction

(b)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{CH}}_{\text{3}}\text{COCl}$, pyridine.

The treatment of leucine with ${\text{CH}}_{\text{3}}\text{COCl}$, pyridine leads to the formation of N-acyl product $\left(2^{\text{ο}}\text{amide}\right)$. The corresponding reaction is shown below.

Figure 3

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 4

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 4.

Interpretation Introduction

(c)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{C}}_6{\text{H}}_5{\text{CH}}_2\text{OH,}{\text{H}}^{+}$.

The reaction between leucine and ${\text{C}}_6{\text{H}}_5{\text{CH}}_2\text{OH,}{\text{H}}^{+}$ involves protection of carbonyl group by as an ester. The corresponding reaction is shown below.

Figure 5

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 6

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 6.

Interpretation Introduction

(d)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{Ac}}_{\text{2}}\text{O}$, pyridine.

The reaction between leucine and ${\text{Ac}}_{\text{2}}\text{O}$, pyridine involves protection of ${\text{NH}}_{\text{2}}$ group by using $\text{Ac}$ group. The corresponding reaction is shown below.

Figure 7

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 8

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 8.

Interpretation Introduction

(e)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is $\text{HCl}\left(\text{1}\text{equiv}\right)$.

The reaction between leucine and $\text{HCl}\left(\text{1}\text{equiv}\right)$, leads to the formation of ammonium chloride salt. The corresponding reaction is shown below.

Figure 9

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 10

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 10.

Interpretation Introduction

(f)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is $\text{NaOH}\left(1\text{equiv}\right)$.

The reaction between leucine and $\text{NaOH}\left(1\text{equiv}\right)$, leads to the formation of carboxylic salt of sodium. The corresponding reaction is shown below.

Figure 11

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 12

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 12.

Interpretation Introduction

(g)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{C}}_6{\text{H}}_5\text{COCl}$, pyridine.

The reaction between leucine and ${\text{C}}_6{\text{H}}_5\text{COCl}$, pyridine leads to the formation of N-acyl product $\left(2^{\text{ο}}\text{amide}\right)$. The corresponding reaction is shown below.

Figure 13

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 14

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 14.

Interpretation Introduction

(h)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\left[{\left({\text{CH}}_{\text{3}}\right)}_3\text{COCO}\right]}_2\text{O,}{\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_3\text{N}$.

The reaction between leucine and ${\left[{\left({\text{CH}}_{\text{3}}\right)}_3\text{COCO}\right]}_2\text{O,}{\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_3\text{N}$ leads to the formation of corresponding N-acylated product $\left(2^{\text{ο}}\text{amide}\right)$. The corresponding reaction is shown below.

Figure 15

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 16

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 16.

Interpretation Introduction

(i)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}+\text{DCC}$.

The structure of product in (d) is shown below.

Figure 8

The reaction between leucine and ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}+\text{DCC}$ involves formation of an amide bond. The corresponding reaction is shown below.

Figure 17

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 18

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 18.

Interpretation Introduction

(j)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}+\text{DCC}$.

The structure of product in (h) is shown below.

Figure 16

The reaction between leucine and ${\text{NH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{COOCH}}_{\text{3}}+\text{DCC}$ involves formation of an amide bond. The corresponding reaction is shown below.

Figure 19

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 20

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 20.

Interpretation Introduction

(k)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is $\text{Fmoc}-\text{Cl,}{\text{Na}}_{\text{2}}{\text{CO}}_{\text{3}},{\text{H}}_{\text{2}}\text{O}$.

The reaction between leucine and $\text{Fmoc}-\text{Cl,}{\text{Na}}_{\text{2}}{\text{CO}}_{\text{3}},{\text{H}}_{\text{2}}\text{O}$ involves protection of an amino group as an $\text{Fmoc}$ derivative. The corresponding reaction is shown below.

Figure 21

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 22

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 22.

Interpretation Introduction

(l)

Interpretation: The organic product formed by the treatment of amino acid leucine with the given reagent is to be drawn.

Concept introduction: The chemical compounds in which carbon is bonded with acidic and basic group along with hydrocarbon side chain are known as amino acids. The amino acids are classified into acidic, basic, polar, non-polar, essential, and non-essential categories. The three word abbreviation or one word abbreviation is used for amino acids.

Answer to Problem 29.40P

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn below.

Explanation of Solution

The given reagent is ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{N}=\text{C}=\text{S}$.

The reaction between leucine and ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{N}=\text{C}=\text{S}$ is an Edman degradation reaction. The reaction occurs between electrophilic carbon of ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{N}=\text{C}=\text{S}$ and nucleophilic ${\text{NH}}_{\text{2}}$ group of given N-terminal acid. The corresponding reaction is shown below.

Figure 23

Thus, the organic product formed by the treatment of amino acid leucine with the given reagent is,

Figure 24

Conclusion

The organic product formed by the treatment of amino acid leucine with the given reagent is drawn in Figure 24.