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Chapter 19: Q22. (page 753)

Question: Draw both enantiomers of each amino acid and label them as Ror S:(a) phenylalanine; (b) methionine.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Step-by-Step SolutionStep 1: Phenylalanine

Phenylalanine has the molecular formula C9H11NO2. It has several isomers, one of which is D-phenylalanine.

02

Methionine

Methionine is an essential amino acid comprising sulfur atoms. It is utilized to cure liver disorders.

03

Enantiomers of methionine and phenylalanine

The groups connected to the stereocenter are prioritized to determine the stereochemistry of a compound. The groups with a higher atomic number are given greater priority than those with a lower atomic number.

A compound is assigned R configuration if it rotates in the clockwise direction and is assigned S configuration if it rotates in the anticlockwise direction.

(a) The enantiomers of phenylalanine are given below:

Enantiomers of phenylalanine

(b) The enantiomers of methionine are given below:

Enantiomers of methionine

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Most popular questions from this chapter

Calculate the isoelectric point for each amino acid.

a. cysteine: pKa (COOH) = 2.05; pKa(伪-NH3+)=10.25

b. methionine: pKa(COOH) = 2.28; pKa(伪-NH3+)=9.21

Question: Depakote, a drug used to treat seizures and bipolar disorder, consists of a mixture of valproic acid [CH3CH2CH22CHCO2H] and its sodium salt. Give IUPAC names for each of these compounds.

Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base.

(a) Explain why the pKafor loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid.

(b) Explain why the pKafor loss of the second proton ( pKa2) is higher for phthalic acid than isophthalic acid.

Draw all resonace strucutres of the conjugate bases formed by removal of the labeled protons (Ha,Hb,andHc)in cyclohexane-1,3-dione and acetanilide. For each compound, rank these protons in order of increasing acidity and explain the order you chose.

a.

b.

Question: Two other commonly used sulfonic acids are methanesulfonic (CH3SO3H)acid and trifluoromethanesulfonic acid (CF3SO3H). Which has the weaker conjugate base? Which conjugate base is the better leaving group? Which of these acids has the higher pka ?
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