Identify how you would make pentylamine from 1-hexanol: OH NH2 The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A. t-BuOK B. 1) O3; 2) DMS C. NaCN D. 1) LiAlH4; 2) H₂O E. H2, Pd F. NaN 3 G. NH 3, NaBH3CN, H+ H. PBr3 I. PCC or DMP

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.54P
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Identify how you would make pentylamine from 1-hexanol:
OH
NH2
The transformation above can be performed with some reagent or combination of the reagents
listed below. Give the necessary reagents in the correct order, as a string of letters (without
spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one
answer.
A. t-BuOK
B. 1) O3; 2) DMS
C. NaCN
D. 1) LiAlH4; 2) H₂O
E. H2, Pd
F. NaN 3
G. NH 3, NaBH3CN, H+
H. PBr3
I. PCC or DMP
Transcribed Image Text:Identify how you would make pentylamine from 1-hexanol: OH NH2 The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A. t-BuOK B. 1) O3; 2) DMS C. NaCN D. 1) LiAlH4; 2) H₂O E. H2, Pd F. NaN 3 G. NH 3, NaBH3CN, H+ H. PBr3 I. PCC or DMP
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