a)b)OHн How might you carry out the following selective transformations? (Note that a protection step may be required, and recall that aldehydes are more reactive than ketones towardnucleophilic addition.)Syntheses may require several steps.Choose the route with the fewest steps.Use letters from the table to list reagents in the order used (first at the left).Example: dagabCd1. excess NaBH42. H3O*1. 1 eq. NaBH42. H3O*1. LiAlH42. H30*aqueous HCIefgReagents1. Li(CH3)2Cu2. H3O+1. CH3MgBr / dry ether2 H3O+HOCH₂CH₂OH/HCIhijTrimethylsilyl chloride /triethylamineCrO3/H3O+Dess-Martin periodinanein CH₂Cl₂

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Answered: a) b) OH معه

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a) b) OH معه

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.42P

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Question

How might you carry out the following selective transformations? (Note that a protection step may be required, and recall that aldehydes are more reactive than ketones toward
nucleophilic addition.)
Syntheses may require several steps.
Choose the route with the fewest steps.
Use letters from the table to list reagents in the order used (first at the left).
Example: dag
a
b
C
d
1. excess NaBH4
2. H3O*
1. 1 eq. NaBH4
2. H3O*
1. LiAlH4
2. H30*
aqueous HCI
e
f
g
Reagents
1. Li(CH3)2Cu
2. H3O+
1. CH3MgBr / dry ether
2 H3O+
HOCH₂CH₂OH/HCI
h
i
j
Trimethylsilyl chloride /
triethylamine
CrO3/H3O+
Dess-Martin periodinane
in CH₂Cl₂

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