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Chapter 21: Q23P (page 1002)

What alkyl halide is used in the acetamidomalonic ester synthesis to prepare a. lysine? b. phenylalanine?

Short Answer

Expert verified

Formation of phenylalanine

Step by step solution

01

Ester synthesis

伪-Bromomalonic ester and potassium phthalimide undergo an SN2 reaction. A proton is easily removed from the a-carbon of N-phthalimidomalonic ester because it is flanked by two carbonyl groups. The resulting carbanion undergoes an SN2reaction with an alkyl halide.

02

Preparation of given amino acid

a)

4-Bromo-1-butanamine is used in the acetamido malonic ester syntheses to prepare lysine which is given as follows:

b)

Benzyl bromide is used in the acetamido malonic ester synthesis to prepare phenylalanine which is represented as follows:

Formation of phenylalanine (b)

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Most popular questions from this chapter

a. Why is the pKaof the glutamate side chain greater than the pKaof the aspartate side chain?

b. Why is the pKa of the arginine side chain greater than the pKa of the lysine side chain?

Which bonds in the backbone of a peptide can rotate freely?

Explain the order of elution (with a buffer of pH 4) of the following pairs of amino acids through a column packed with Dowex 50 (Figure 21.3):

a. aspartate before serine c. valine before leucine

b. serine before alanine d. tyrosine before phenylalanine

alpha- Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.

a. Draw the structures of the two intermediates formed in this reaction.

b. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?

c. What aldehyde is needed to prepare isoleucine?

Draw the predominant form for glutamate in a solution with the following pH:

a.0 b. 3 c. 6 d. 11
See all solutions

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