10.2 Synthesis of alpha-amino acids

Question 1

strecker synthesis

Answer 1

a method to synthesize alpha amino acids

Question 2

aminonitrile

Answer 2

a compound containing both an amino group (NH2) and a nitrile group

Question 3

nitrile functional group

Answer 3

Question 4

the R group on the starting aldehyde in strecker synthesis…

Answer 4

IS the R group on the desired amino acid

Question 5

strecker synthesis: step 1

Answer 5

starts with aldehyde, ammonium chloride (NH4Cl), and potassium cyanide (KCN)

1) carbonyl oxygen is protonated
2) ammonia attacks the carbonyl carbon
3) the N in the molecule attacks the carbon, forming a double bond and kicking off the water molecule, forming an imine
4) CN- anion attacks, forming a nitrile group

final molecule: aminonitrile

Question 6

strecker synthesis: step 2

Answer 6

the nitrile nitrogen is protonated

water molecule attacks TWICE

a carbonyl is formed, kicking off ammonia (LG) and creating the carboxyl functional group

OH+ is deprotonated

Question 7

strecker synthesis produces amino acids of which configuration?

Answer 7

a racemic mixture of BOTH L- and D-amino acids

Question 8

gabriel malonic-ester synthesis

Answer 8

1) starts with potassium phthalimide and diethyl bromomalonate

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