ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 5, Problem 5.28P

The amino acid ( S ) -alanine has the physical characteristics listed under the structure.

Chapter 5, Problem 5.28P, Problem 5.28 The amino acid  has the physical characteristics listed under the

(S)-alanine

[ α ] = + 8.5

mp = 297 ° C

a. What is the melting point of ( R ) -alanine ?

b. How does the melting point of a racemic mixture of ( R ) - and ( S ) -alanine compare to the melting point of ( S ) -alanine ?

c. What is the specific rotation of ( R ) -alanine , recorded under the same conditions as the reported rotation of ( S ) -alanine ?

d. What is the optical rotation of a racemic mixture of ( R ) - and ( S ) -alanine ?

e. Label each of the following as optically active or inactive: a solution of pure ( S ) -alanine ; an equal mixture of ( R ) - and ( S ) -alanine ; a solution that contains 75 % ( S ) - and 25 % ( R ) -alanine .

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The melting point of (R)-alanine is to be predicted.

Concept introduction: Enantiomers are the stereoisomers that have exactly opposite R,S notations. Diastereomers are the stereoisomers that have the opposite R,S notations for at least one stereogenic center and the same R,S notations for at least one stereogenic center. Enantiomers have identical physical properties, whereas diastereomers have different physical properties.

Answer to Problem 5.28P

The melting point of (R)-alanine is 297°C.

Explanation of Solution

The given melting point of (S)-alanine is 297°C. The (R)-alanine, and (S)-alanine are the enantiomers. Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. Therefore, the melting point of (R)-alanine is also 297°C.

Conclusion

The melting point of (R)-alanine is 297°C.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The melting point of a racemic mixture of (R)-and(S)-alanine is to be compared with the melting point of (S)-alanine.

Concept introduction: Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. A racemic mixture is obtained when (R)-and(S) enantiomers are mixed in equal amount. Their racemic mixture possess different physical properties than parent one.

Answer to Problem 5.28P

The melting point of a racemic mixture of (R)-and(S)-alanine is different with the melting point of (S)-alanine.

Explanation of Solution

The given melting point of (S)-alanine is 297°C. The (R)-alanine, and (S)-alanine are the enantiomers. Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. A racemic mixture is obtained when (R)-and(S) enantiomers are mixed in equal amount. Their racemic mixture possess different physical properties than parent one.

Therefore, the melting point of a racemic mixture of (R)-and(S)-alanine is different with the melting point of (S)-alanine.

Conclusion

The melting point of a racemic mixture of (R)-and(S)-alanine is different with the melting point of (S)-alanine.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The specific rotation of (R)-alanine is to be predicted.

Concept introduction: Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. Their specific rotation values are opposite in sign but equal in magnitude, when they are recorded under same condition.

Answer to Problem 5.28P

The specific rotation of (R)-alanine is 8.5.

Explanation of Solution

The specific rotation of (S)-alanine is +8.5. The (R)-alanine, and (S)-alanine are the enantiomers. Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. Their specific rotation values are opposite in sign but equal in magnitude, when they are recorded under same condition.

Thus, the specific rotation of (R)-alanine is 8.5.

Conclusion

The specific rotation of (R)-alanine is 8.5.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The optical rotation of a racemic mixture of (R)-and(S)-alanine is to be calculated.

Concept introduction: Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. A racemic mixture is obtained when (R)-and(S) enantiomers are mixed in equal amount.

Answer to Problem 5.28P

The optical rotation of a racemic mixture of (R)-and(S)-alanine is zero.

Explanation of Solution

The specific rotation of (S)-alanine is +8.5.

The specific rotation of (R)-alanine is 8.5.

The (R)-alanine, and (S)-alanine are the enantiomers. Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. A racemic mixture is obtained when (R)-and(S) enantiomers are mixed in equal amount.

Thus, the optical rotation of a racemic mixture of (R)-and(S)-alanine is zero (8.5+8.5=0).

Conclusion

The optical rotation of a racemic mixture of (R)-and(S)-alanine is zero.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The solutions of pure (S)-alanine, an equal mixture of (R)-and(S)-alanine, 75%(S)-and25%(R)-alanine are to be labeled as optically active or inactive.

Concept introduction: Enantiomers are the stereoisomers that have exactly opposite R,S notations. They possess identical physical properties. A racemic mixture is obtained when (R)-and(S) enantiomers are mixed in equal amount. Their racemic mixture possess different physical properties than parent one.

Answer to Problem 5.28P

The pure (S)-alanine is labeled as optically active, an equal mixture of (R)-and(S)-alanine is labeled as optically inactive, 75%(S)-and25%(R)-alanine is labeled as optically active.

Explanation of Solution

The pure (S)-alanine is an enantiomer. Enantiomers are optically active compounds. Thus, (S)-alanine is optically active compound.

A racemic mixture is obtained when (R)-and(S) enantiomers are mixed in equal amount. Thus, an equal mixture of (R)-and(S)-alanine is optically inactive.

A 75%(S)-and25%(R)-alanine solution is optically active. Because, in solution 25%(R)-alanine cancel only 25%(S)-alanine and still 50% of (S)-alanine is left. Therefore, 75%(S)-and25%(R)-alanine solution is optically active.

Thus, the pure (S)-alanine is labeled as optically active, an equal mixture of (R)-and(S)-alanine is labeled as optically inactive, 75%(S)-and25%(R)-alanine is labeled as optically active.

Conclusion

The pure (S)-alanine is labeled as optically active, an equal mixture of (R)-and(S)-alanine is labeled as optically inactive, 75%(S)-and25%(R)-alanine is labeled as optically active.

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Students have asked these similar questions
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Chapter 5 Solutions

ORGANIC CHEMISTRY

Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Label each compound as R or S.Ch. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Problem 5.18 Compounds E and F are two isomers of...Ch. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Which of the following cyclic molecules are meso...Ch. 5 - Prob. 5.26PCh. 5 - Prob. 5.27PCh. 5 - Problem 5.28 The amino acid has the physical...Ch. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Prob. 5.38PCh. 5 - Prob. 5.39PCh. 5 - 5.40 Determine if each compound is identical to or...Ch. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Prob. 5.46PCh. 5 - Label each stereogenic center as R or S. a. c. e....Ch. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.52PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Prob. 5.56PCh. 5 - Prob. 5.57PCh. 5 - Prob. 5.58PCh. 5 - 5.59 Explain each statement by referring to...Ch. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 - Prob. 5.66PCh. 5 - 5.67 Artemisinin and mefloquine are widely used...Ch. 5 - 5.68 Saquinavir (trade name Invirase) is a...Ch. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Prob. 5.72PCh. 5 - Problem 5.73 An acid-base reaction of with a...
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