Select the methods of synthesis that could be used to make the following amino acid. These reactions are presented in section 21.6 of your text. I have provided them in abbreviated generic form below in case you might find this helpful. Note that I have edited the Strecker synthesis to allow for the possibility of a ketone instead of an aldehyde as the starting material. (The text shows only aldehydes as reactants.) H,N, 1) Br,, PB13 Hell-Volhard-Zelinski R 2) H,O 3) excess NH, `OH HO, NH, R 1) excess NH, Reductive amination `OH ОН 2) H2, Pd/C NH, 1) NH3 R Strecker `OH 2) HCN R 3) HC, Н,О, Д NH, 1) potassium phthalimide R' Phthalimidomalonic ester RO `OR `OH 2) RO© Br 3) R'-Br NH2 4) HC, H,О, Д O Hell-Volhard-Zelinski (HVZ) O Reductive amination O Strecker O Phthalimidomalonic ester

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Chapter1: Chemical Foundations
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Select the methods of synthesis that could be used to make the following amino acid. These
reactions are presented in section 21.6 of your text. I have provided them in abbreviated generic
form below in case you might find this helpful. Note that I have edited the Strecker synthesis to
allow for the possibility of a ketone instead of an aldehyde as the starting material. (The text shows
only aldehydes as reactants.)
H,N,
OH
CH,
1) Br,, PBr3
Hell-Volhard-Zelinski
R
R.
2) H,O
3) excess NH3
`OH
OH
NH,
1) excess NH3
Reductive amination
ОН
НО.
2) H2, Pd/C
NH,
R'
1) NH3
R
Strecker
HO,
2) HCN
R
`R'
3) HCІ, Н,0, д
NH,
1) potassium phthalimide
R'
Phthalimidomalonic ester
RO
OR
2) RO©
НО.
Br
3) R'-Br
NH,
4) НCІ, H,0, Д
O Hell-Volhard-Zelinski (HVZ)
O Reductive amination
O Strecker
O Phthalimidomalonic ester
Transcribed Image Text:Select the methods of synthesis that could be used to make the following amino acid. These reactions are presented in section 21.6 of your text. I have provided them in abbreviated generic form below in case you might find this helpful. Note that I have edited the Strecker synthesis to allow for the possibility of a ketone instead of an aldehyde as the starting material. (The text shows only aldehydes as reactants.) H,N, OH CH, 1) Br,, PBr3 Hell-Volhard-Zelinski R R. 2) H,O 3) excess NH3 `OH OH NH, 1) excess NH3 Reductive amination ОН НО. 2) H2, Pd/C NH, R' 1) NH3 R Strecker HO, 2) HCN R `R' 3) HCІ, Н,0, д NH, 1) potassium phthalimide R' Phthalimidomalonic ester RO OR 2) RO© НО. Br 3) R'-Br NH, 4) НCІ, H,0, Д O Hell-Volhard-Zelinski (HVZ) O Reductive amination O Strecker O Phthalimidomalonic ester
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