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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.

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Smells like celery leaves

Smells like licorice

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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 shrub ma huang (Section 5.4 A) contains two biologically active stereoisomers-ephedrine and pseudoephedrine-with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once popular combination drug used by body builders to increase energy and alertness, while pseudoephedrine is a nasal decongestant.

a. Draw the structure of naturally occurring (โ€“)-ephedrine, which has the 1R,2Sconfiguration.

b. Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2Sconfiguration.

c. How are ephedrine and pseudoephedrine related?

d. Draw all other stereoisomers of (โ€“)-ephedrine and (+)-pseudoephedrine and give the R,Sdesignation for all stereogenic centers.

e. How is each compound drawn in part (d) related to (โ€“)-ephedrine?

Compare the physical properties of the three stereoisomers of 1,3-dimethylcyclopenatane.

  1. How do the boiling points of A and B compare? What about A and C?
  2. Characterize a solution of each of the following as optically active or optically inactive: pure A; pure B; pure C; an equal mixture of A and B; an equal mixture of A and C.
  3. A reaction forms a 1:1:1 mixture of A, B, and C. If this mixture is distilled, how many fractions would be obtained? Which fractions would be optically active and which would be optically inactive?

Consider Newman projections (Aโ€“D) for four-carbon carbohydrates. How is each pairof compounds related: (a) A and B; (b) A and C; (c) A and D; (d) C and D? Choose fromidentical molecules, enantiomers, or diastereomers.

What is the ee for each of the following mixtures of enantiomers A and B?

a. 95% A and 5% B

b. 85% A and 15% B

Cellulose is water insoluble, despite its many OH groups. Considering its three-dimensional structure, why do you think this is so?

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