The conformations of the two enanatiomers of alanine are to be drawn using the standard convention of solid, wedged and dashed lines. Concept introduction: For representing the conformations of a molecule wedge and dash projection is used. The three dimentional structure of the molecule is represented by three types of lines i) solid lines represent bonds that are in the plane of the paper ii) dashed lines represent bonds that extend away from the viewer iii) wedge shaped lines represent bonds that face the viewer. To draw: The conformations of the two enanatiomers of alanine using the standard convention of solid, wedged and dashed lines.

Question

I'm confused as to why the chiral centers are the was they are. I understand that the horizontal lines are wedged and vertical are dashed. Wouldn't the first priority be the carboxylic acid, then alcohol, the carbon, and then the hydrogen? The book is saying that one method is to keep two of the straight lines and pick one group to be dashed and one to be wedged. Then switch the last priority group (H) with whatever group you chose to be on the dash. Whatever configuration you get, make it the opposite since you switched groups. And when I use this method I end up getting S when the top one should be R.

Answer 1

Question

Chapter 5.2, Problem 3P

Interpretation Introduction

Interpretation:

The conformations of the two enanatiomers of alanine are to be drawn using the standard convention of solid, wedged and dashed lines.

Concept introduction:

For representing the conformations of a molecule wedge and dash projection is used. The three dimentional structure of the molecule is represented by three types of lines i) solid lines represent bonds that are in the plane of the paper ii) dashed lines represent bonds that extend away from the viewer iii) wedge shaped lines represent bonds that face the viewer.

To draw:

The conformations of the two enanatiomers of alanine using the standard convention of solid, wedged and dashed lines.

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I'm confused as to why the chiral centers are the was they are. I understand that the horizontal lines are wedged and vertical are dashed. Wouldn't the first priority be the carboxylic acid, then alcohol, the carbon, and then the hydrogen? The book is saying that one method is to keep two of the straight lines and pick one group to be dashed and one to be wedged. Then switch the last priority group (H) with whatever group you chose to be on the dash. Whatever configuration you get, make it the opposite since you switched groups. And when I use this method I end up getting S when the top one should be R.

I have already drawn helicene as an example but I am stuck on thinking of two other compounds. I know that an asymmetrically substituted carbon atom has 4 different substituents attached to the carbon. But, I am confused about finding other structures that are still chiral but do not have an asymmetrically substituted carbon atom.

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