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Chapter 5: Q.35 (page 204)

Like carvone, the two enantiomers of celery ketone smell differently. The R enantiomer smells like celery leaves, whereas the S enantiomer smells like licorice. Draw each enantiomer and assign its odor.

Short Answer

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Smells like celery leaves

Smells like licorice

Step by step solution

01

Definition of enantiomers

Enantiomers are the two stereoisomers of a compound which are the non-superimposable mirror images of each other. The enantiomers of a compound have the same physical properties, such as melting points, boiling points, and solubility.

Both the enantiomers of a compound are able to rotate the plane-polarized light to the same extent but in opposite directions.

02

Enantiomers of celery ketone

The celery ketone has two enantiomers R and S. The structures of the enantiomers are shown below:

Smells like celery leaves

Smells like licorice

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Most popular questions from this chapter

The facts in Section 5.4A can be used to locate stereogenic centers in any molecule, no matter how complicated. Always look for carbons surrounded by four different groups. With this in mind, locate the four stereogenic centers in aliskiren, a drug introduced in 2007 for the treatment of hypertension.

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

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.

Which group in each pair is assigned the higher priority in R,S nomenclature?

  1. -CD3,-CH3
  2. localid="1648446360910" -CH(CH3)2,-CH2OH
  3. localid="1648447310055" -CH2Cl,-CH2CH2CH2Br
  4. -CH2NH2,-NHCH3

The [伪] of pure quinine, an antimalarial drug, is 鈥�165.

a. Calculate the ee of a solution with the following [伪] values: 鈥�50, 鈥�83, and 鈥�120.

b. For each ee, calculate the percent of each enantiomer present.

c. What is [伪] for the enantiomer of quinine?

d. If a solution contains 80% quinine and 20% of its enantiomer, what is the ee of the solution?

e. What is [伪] for the solution described in part (d)?

Locate the stereogenic centers in each Newman projection and label each center as R or S.

a.

b.
See all solutions

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