Complete the statements by providing the reagents necessary to complete each step of the synthesis. 5-phenyl1pentanol reacted with 5phenylpentanal, which was converted to 6-phenylhexan-2-ol by treatment with oxidation of 6-phenylhexan-2-ol y with with to yield 2-hydroxy-2-methyl-6-phenylhexanenitrile as the final product. 1) NaCN, H₂SO4 2) K2Cr2O7; H₂SO4 ,water 3) HgSO4 H2SO4 4) i) CH3MgBr, Ether ii) H3O+ 5) B2H6, H₂O 6) Br2 CCl4 7) CH3NH2, H* 8) (CH3CH2CH2)2CuLi 9) Sia2BH,H2O2, NaOH 10) SOCI2 or PC|5 11) (i)LIAIH4 (ii) H3O+ 12)HCI, H₂O, heat 13) NBS, C- 14) C6H5L 15) Zn(H 16) xs C

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.52P
Question
Complete the statements by providing the reagents necessary to complete each step of the synthesis. 5-phenyl1pentanol reacted with
5phenylpentanal, which was converted to 6-phenylhexan-2-ol by treatment with
oxidation of 6-phenylhexan-2-ol yi
to yield 2-hydroxy-2-methyl-6-phenylhexanenitrile as the final product.
with with
1) NaCN, H₂SO4
2) K2Cr2O7; H₂SO4 ,water
3) HgSO4 H₂SO4
4) i) CH3MgBr, Ether ii) H3O+
5) B2H6, H₂O
6) Br2 CCl4
7) CH3NH2, H*
8) (CH3CH₂CH2)2CULI
9) Sia2BH,H202, NaOH
10) SOCI2 or PCl5
11) (i)LIAIH4 (ii) H3O*
12)HCI, H₂O, heat
13) NBS, C
14) C6H5
15) Zn(H
16) xs C
Transcribed Image Text:Complete the statements by providing the reagents necessary to complete each step of the synthesis. 5-phenyl1pentanol reacted with 5phenylpentanal, which was converted to 6-phenylhexan-2-ol by treatment with oxidation of 6-phenylhexan-2-ol yi to yield 2-hydroxy-2-methyl-6-phenylhexanenitrile as the final product. with with 1) NaCN, H₂SO4 2) K2Cr2O7; H₂SO4 ,water 3) HgSO4 H₂SO4 4) i) CH3MgBr, Ether ii) H3O+ 5) B2H6, H₂O 6) Br2 CCl4 7) CH3NH2, H* 8) (CH3CH₂CH2)2CULI 9) Sia2BH,H202, NaOH 10) SOCI2 or PCl5 11) (i)LIAIH4 (ii) H3O* 12)HCI, H₂O, heat 13) NBS, C 14) C6H5 15) Zn(H 16) xs C
nts necessary to complete each step of the synthesis. 5-phenyl1pentanol reacted with
oxidation of 6-phenylhexan-2-ol yielded 6-phenylhexan-2-one, which was treated
Thexan-2-ol by treatment with
vdroxy-2-methyl-6-phenylhexanenitrile
2H6, H₂O
CC14
WH2, H*
CH₂CH₂)2 CuLi
as the final product.
9) Sia2BH,H₂O2, NaOH
10) SOCI2 or PC15
11) (1)LIAIH4 (ii) H3O*
12)HCI, H₂O, heat
13) NBS, CCI14
14) C6H5Li, Ether
15) Zn(Hg) HCI
16) xs CH3CH₂MgBr
to form
17)(CH3)2NH; H*
18) (CH₂OH)2; H+
19) 95 % H₂SO4, heat
20) PCC
Transcribed Image Text:nts necessary to complete each step of the synthesis. 5-phenyl1pentanol reacted with oxidation of 6-phenylhexan-2-ol yielded 6-phenylhexan-2-one, which was treated Thexan-2-ol by treatment with vdroxy-2-methyl-6-phenylhexanenitrile 2H6, H₂O CC14 WH2, H* CH₂CH₂)2 CuLi as the final product. 9) Sia2BH,H₂O2, NaOH 10) SOCI2 or PC15 11) (1)LIAIH4 (ii) H3O* 12)HCI, H₂O, heat 13) NBS, CCI14 14) C6H5Li, Ether 15) Zn(Hg) HCI 16) xs CH3CH₂MgBr to form 17)(CH3)2NH; H* 18) (CH₂OH)2; H+ 19) 95 % H₂SO4, heat 20) PCC
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