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Ch.5 - Stereochemistry
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
5장, 문제 6a,b

Star (*) each asymmetric carbon atom in the following examples, and determine whether it has the (R) or (S) configuration.
(a) Molecular structure showing an asymmetric carbon atom with groups labeled for R and S configuration determination.
(b) Structural formula of a chiral carbon atom with attached groups, indicating R and S configurations.

검증된 단계별 안내
1
Step 1: Identify the asymmetric carbon atom in each molecule. An asymmetric carbon is a carbon atom bonded to four different groups. In both molecules, the central carbon atom is bonded to four distinct groups, making it asymmetric.
Step 2: Assign priorities to the substituents attached to the asymmetric carbon based on the Cahn-Ingold-Prelog priority rules. The rules state that the atom with the highest atomic number gets the highest priority. If two atoms are the same, consider the atoms directly bonded to them.
Step 3: Orient the molecule so that the lowest priority group (usually hydrogen) is pointing away from you. This ensures that you can correctly determine the configuration.
Step 4: Determine the order of the remaining three groups (1, 2, 3) based on their priorities. Trace a path from the highest priority group (1) to the second (2) and then to the third (3). If the path is clockwise, the configuration is (R). If the path is counterclockwise, the configuration is (S).
Step 5: Repeat the process for both molecules, ensuring that you carefully follow the priority rules and orientation guidelines to assign the correct (R) or (S) configuration for each asymmetric carbon.

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주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Chirality

Chirality refers to the geometric property of a molecule that makes it non-superimposable on its mirror image. A chiral molecule typically contains an asymmetric carbon atom, which is bonded to four different substituents. This property is crucial in organic chemistry as it affects the molecule's interactions and biological activity.
추천 영상:
가이드 코스
05:10
What is chirality?

R and S Configuration

The R and S configuration system is used to describe the spatial arrangement of substituents around a chiral center. To assign R or S, the substituents are ranked based on atomic number, with the highest priority assigned first. The configuration is determined by the orientation of the lowest priority group; if it is positioned at the back and the sequence of the other groups is clockwise, it is R; if counterclockwise, it is S.
추천 영상:
가이드 코스
03:07
R and S Naming- Step 4

Cahn-Ingold-Prelog Priority Rules

The Cahn-Ingold-Prelog priority rules are a set of guidelines used to assign priority to substituents attached to a chiral center. These rules state that higher atomic number atoms take precedence over lower ones, and in cases of ties, the next atoms in the substituent chain are considered. Understanding these rules is essential for accurately determining the R or S configuration of chiral molecules.
추천 영상:
가이드 코스
01:48
Why stereoisomers need their own naming system.
관련 실천
교과서 질문

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).

(a)

(b)

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교과서 질문
b. Draw the six stereoisomers of octa-2,4,6-triene. Explain why there are only six stereoisomers, rather than the eight we might expect for a compound with three stereogenic double bonds.
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교과서 질문

Star (*) each asymmetric carbon atom in the following examples, and determine whether it has the (R) or (S) configuration.

(i)

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교과서 질문

For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral.

(d) 1,2-dichloropropane

(e)

1828
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교과서 질문

For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral.

(h)

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교과서 질문
A solution of pure (S)-2-iodobutane ([α] = +15.90° ) in acetone is allowed to react with radioactive iodide, 131I-, until 1.0% of the iodobutane contains radioactive iodine. The specific rotation of this recovered iodobutane is found to be +15.58°. a. Determine the percentages of (R)- and (S)-2-iodobutane in the product mixture.
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