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Ch.5 - Stereochemistry
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
모든 교과서Wade 9th EditionCh.5 - Stereochemistry문제 17a,b
5장, 문제 17a,b

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.
(a) (S)-propane-1,2-diol
(b) (R)-2-bromobutan-1-ol

검증된 단계별 안내
1
Understand the Fischer projection: A Fischer projection is a two-dimensional representation of a molecule where the vertical lines represent bonds going away from the viewer (into the plane), and the horizontal lines represent bonds coming toward the viewer (out of the plane). The carbon chain is placed vertically, with the highest-priority functional group at the top.
For (S)-propane-1,2-diol: Start by identifying the structure of propane-1,2-diol. It has three carbon atoms, with hydroxyl (-OH) groups attached to the first and second carbons. Assign the stereochemistry (S) to the second carbon, which is the chiral center. Use the Cahn-Ingold-Prelog priority rules to determine the configuration.
Draw the Fischer projection for (S)-propane-1,2-diol: Place the carbon chain vertically, with the first carbon (containing the -OH group) at the top. The second carbon (chiral center) will have the -OH group and hydrogen on the horizontal bonds. Arrange the groups such that the configuration matches the (S)-stereochemistry.
For (R)-2-bromobutan-1-ol: Identify the structure of 2-bromobutan-1-ol. It has four carbon atoms, with a bromine atom attached to the second carbon and a hydroxyl (-OH) group attached to the first carbon. The second carbon is the chiral center. Assign the stereochemistry (R) to the second carbon using the Cahn-Ingold-Prelog priority rules.
Draw the Fischer projection for (R)-2-bromobutan-1-ol: Place the carbon chain vertically, with the first carbon (containing the -OH group) at the top. The second carbon (chiral center) will have the bromine atom and hydrogen on the horizontal bonds. Arrange the groups such that the configuration matches the (R)-stereochemistry.

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주요 개념

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

Fischer Projections

Fischer projections are a two-dimensional representation of three-dimensional organic molecules, particularly useful for depicting stereochemistry. In these diagrams, vertical lines represent bonds that project behind the plane of the page, while horizontal lines represent bonds that project out of the page. This format is especially helpful for visualizing the configuration of chiral centers in molecules.
추천 영상:
09:56
Monosaccharides - Drawing Fischer Projections

Chirality and Stereochemistry

Chirality refers to the geometric property of a molecule having non-superimposable mirror images, often due to the presence of asymmetric carbon atoms. Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. Understanding the (R) and (S) nomenclature is crucial for accurately representing the stereochemistry of compounds in Fischer projections.
추천 영상:
가이드 코스
1:21
Polymer Stereochemistry Example 1

IUPAC Nomenclature

IUPAC nomenclature is a systematic method for naming organic chemical compounds, providing a unique name that conveys the structure of the molecule. It includes rules for identifying the longest carbon chain, numbering the carbon atoms, and designating functional groups. Familiarity with IUPAC rules is essential for correctly interpreting and drawing structures like (S)-propane-1,2-diol and (R)-2-bromobutan-1-ol in Fischer projections.
추천 영상:
03:43
The different parts of an IUPAC name
관련 실천
교과서 질문

For each Fischer projection,

1. make a model.

2. draw the mirror

3.. determine whether the mirror is the same as, or different from, the original ­structure.

4. draw any mirror planes of symmetry that are apparent from the Fischer projections.

(c)

(d)

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교과서 질문

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.

(c) (S)-1,2-dibromobutane

(d) (R)-butan-2-ol

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교과서 질문

For each set of examples, make a model of the first structure, and indicate the relationship of each of the other structures to the first structure. Examples of relationships: same compound, enantiomer, structural isomer.

(a)

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교과서 질문

Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.

(e)

1397
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교과서 질문

For each set of examples, make a model of the first structure, and indicate the relationship of each of the other structures to the first structure. Examples of relationships: same compound, enantiomer, structural isomer.

(c)

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교과서 질문

Draw three-dimensional representations of the following compounds. Which have asymmetric carbon atoms? Which have no asymmetric carbons but are chiral anyway? Use your models for parts (a) through (d) and any others that seem unclear.

(g)

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