Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 5.5, Problem 5.11P

(a)

Interpretation Introduction

To determine: The enantiomer of carvone that smells like spearmint.

Interpretation: The enantiomer of carvone that smells like spearmint is to be identified.

Concept introduction: A chiral carbon atom is attached to four different atoms or group of atoms and shows a tetrahedral geometry. The mirror image of a chiral compound is non super imposable. The two different forms in which a single chiral carbon can exist are referred as enantiomers. The number of enantiomers of a molecule depends on the number of chiral centers.

(b)

Interpretation Introduction

To determine: Whether the (R) or (S) enantiomer of carvone smells like spearmint.

Interpretation: Whether the (R) or (S) enantiomer of carvone smells spearmint is to be identified.

Concept introduction: A chiral carbon atom is attached to four different atoms or group of atoms and shows a tetrahedral geometry. The mirror image of a chiral compound is non-super imposable. The two different forms in which a single chiral carbon can exist are referred as enantiomers. The number of enantiomers of a molecule depends on the number of chiral centers.

(c)

Interpretation Introduction

To determine: The information that can be added to the answers in (a) and (b) with the help of the given drawings of carvone.

Interpretation: The information that can be added to the answers in (a) and (b) with the help of the given drawings of carvone is to be stated.

Concept introduction: A chiral carbon atom is attached to four different atoms or group of atoms and shows a tetrahedral geometry. The mirror image of a chiral compound is non-super imposable. The two different forms in which a single chiral carbon can exist are referred as enantiomers. The number of enantiomers of a molecule depends on the number of chiral centers.

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3. Write and construct the compound (2St 3S)-2,3-dibromobutane (13). Identify chiral carbons and make sure of the stereochemistry of chiral carbons. Draw and build the reflection of 13 (14). what is the name of 14? What is the ratio between 13 and 14? Draw and build a diastereomer for 13 (15) assigning the appropriate configuration for chiral centers. Draw and build the reflection of 15 (16). What is the ratio between 15 and 16? Between 13 and 15? Between 14 and 15?
pt. 4: Molecular Models: Stereoisomers me: 4. Using the model of 2-bromobutane representing the R enantiomer from 4., switch any two groups on the chiral carbon. Compare this to your S enantiomer from 4. a. Are they the same or different? b. Are they the same or enantiomers? C. Now switch any pair of groups around the chiral carbon of the "switched" model again! Compare the "double-switched" model with the other unmodified S molecule from 4. Are they enantiomers or are they identical? С. Shown below is the Fisher projection of (R)-2-bromo-(S)-3-chlorobutane. ne mirror image of this stereoisomer and assign the RIS configurations of iral carbons for both isomers. е ll er
The [α] of pure quinine, an antimalarial drug, is −165. a.Calculate the ee of a solution with the following [α] values: −50, −83, and −120. b. For each ee, calculate the percent of each enantiomer present. c.What is [α] 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 [α] for the solution described in part (d)?
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