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

Chemistry: Principles and Reactions
8th Edition
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:William L. Masterton, Cecile N. Hurley
Chapter23: Organic Polymers, Natural And Synthetic
Section: Chapter Questions
Problem 31QAP: On complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one...
icon
Related questions
icon
Concept explainers
Question
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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 4 images

Blurred answer
Knowledge Booster
Proteins
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
World of Chemistry
World of Chemistry
Chemistry
ISBN:
9780618562763
Author:
Steven S. Zumdahl
Publisher:
Houghton Mifflin College Div
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic And Biological Chemistry
Organic And Biological Chemistry
Chemistry
ISBN:
9781305081079
Author:
STOKER, H. Stephen (howard Stephen)
Publisher:
Cengage Learning,
General, Organic, and Biological Chemistry
General, Organic, and Biological Chemistry
Chemistry
ISBN:
9781285853918
Author:
H. Stephen Stoker
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning