Amino Acid Synthesis

Question 1

During Gabriel synthesis of primary amines, the secondary carbon serves as?

Answer 1

Electrophile — nitrogen on Phthalimide acts like nucleophile > attacking electrophilic secondary carbon of alkyl halide

Question 2

Overall Idea of Gabriel synthesis

Answer 2

Protected amide and carbonyl (pthalimide)

- SN2

Question 3

Step 1 Gabriel synthesis:

Answer 3

Alkylation: central C and R group

Question 4

step 2 Gabriel synthesis

Answer 4

Hydrolysis: protecting group of amine is hydrolyzed

Question 5

step 3 Gabriel synthesis

Answer 5

Decarboxylation: heat removes COOH group (extra group)

Question 6

Overall idea of strecker synthesis

Answer 6

Aldehyde/ketone > reaction > amino acid

Question 7

Step 1 strecker

Answer 7

Ald/ketone + NH3 with acid > C=N, ald/ketone is protonated

Question 8

Step 2 strecker

Answer 8

C=n and CN- formed > alpha amino nitrile

Question 9

Step 3 strecker

Answer 9

Hydrolysis of nitrile forms amino acid