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Chapter 4: Q30P (page 161)

What is the configuration of the following compounds? (Use the given structures to answer the question.)

a. (-)-glyceric acid


b.(+)-isoserine


c. (+)-lactic acid

Short Answer

Expert verified
  1. R-configuration
  2. R-configuration
  3. R-configuration

Step by step solution

01

The R/S system of nomenclature.

Cahn, Ingold, and Prelog devised a mechanism that, no matter which way we look at the molecule, always yields the same name (unlike the wedge and dash notation).

As a result, this system is also known as the absolute Configuration or, more popularly, the R and S system.

02

Subpart (a) To determine the configuration of (-)-glyceric acid.

  • Because the group with thelowest priority is on the hatched wedge.
  • The arrow drawn from the COOH group to thegroup isclockwise.
  • (-)-glyceric acid has the R configuration.
03

Subpart (b) To determine the configuration of (+)-isoserine.

  • Because the group with the lowest priority is on the hatched wedge.
  • The arrow drawn from the COOH group to the group is clockwise.
  • (+)-isoserinehas the R configuration.
04

Subpart (c) To determine the configuration of (+)-lactic acid.

  • Because the group with the lowest priority is on the hatched wedge.
  • The arrow drawn from the COOH group to the group isclockwise.
  • (+)-lactic acidhas theR configuration.

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Most popular questions from this chapter

A sample of (S)-(+)-lactic acid was found to have an enantiomeric excess of 72%. How much Risomer is present in the sample?

Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?

Question:

a. Draw all the isomers with molecular formula C6H12 that contain a cyclobutane ring. (Hint: There are seven.)

b. Name the compounds without specifying the configuration of any asymmetric centers.

c. Identify

1. constitutional isomers 2. Stereoisomers 3. cis鈥搕rans isomers 4. chiral compounds

5. achiral compounds 6. Meso compounds 7. Enantiomers 8. diastereomers

Convert the Fischer projection to a perspective formula.

1-Bromo-2-methylcyclopentane has four pairs of diastereomers. Draw the four pairs
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