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Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471당신이 사용하는 게 아니라요?교과서 변경
26장, 문제 7c

Draw Fischer projections of the following molecules.
(c) Fischer projection of a molecule showing an amine group (NH2) and a phenyl group (Ph) attached to a carbon chain.

검증된 단계별 안내
1
Step 1: Understand the structure provided. The molecule has an amine group (NH₂) attached to a chiral carbon, along with a phenyl group (Ph) and a methyl group (CH₃). The dashed wedge indicates that the NH₂ group is oriented away from the viewer.
Step 2: Recall the rules for drawing Fischer projections. In a Fischer projection, the horizontal lines represent bonds coming out of the plane (towards the viewer), and the vertical lines represent bonds going into the plane (away from the viewer). The chiral carbon is at the intersection of the lines.
Step 3: Assign priorities to the substituents based on the Cahn-Ingold-Prelog rules. The NH₂ group has the highest priority, followed by the phenyl group (Ph), the methyl group (CH₃), and finally the hydrogen atom.
Step 4: Orient the molecule so that the lowest priority group (hydrogen) is on the vertical line pointing away from the viewer. This ensures the correct stereochemistry is represented in the Fischer projection.
Step 5: Draw the Fischer projection. Place the NH₂ group and the phenyl group on the horizontal lines (coming out of the plane), and the methyl group and hydrogen on the vertical lines (going into the plane). Ensure the stereochemistry matches the original molecule.

비슷한 문제에 대한 검증된 영상 답변:

이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
영상 길이:
2m

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 towards the viewer. This format is especially common for carbohydrates and amino acids, allowing for easy visualization of chiral centers and their configurations.
추천 영상:
09:56
Monosaccharides - Drawing Fischer Projections

Chirality and Stereocenters

Chirality refers to the property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of one or more stereocenters. A stereocenter is typically a carbon atom bonded to four different substituents, leading to two possible configurations (R and S). Understanding chirality is crucial for accurately drawing Fischer projections, as it determines the spatial arrangement of the substituents around the stereocenter.
추천 영상:
02:25
Determining Chirality using Stereocenter

Configuration Notation (R/S)

The R/S notation is a system used to specify the absolute configuration of chiral centers in molecules. To assign R (rectus) or S (sinister) configuration, one must prioritize the substituents attached to the stereocenter based on atomic number, with higher atomic numbers receiving higher priority. This systematic approach is essential for accurately representing the stereochemistry in Fischer projections and understanding the molecule's reactivity and interactions.
추천 영상:
03:07
R and S Naming- Step 4