HO H2SO4 (а) Н,С- heat `C,Hs (CH3)3COOH, OsO4(cat) (b) (CII3);COII, IIO- 1. B,H6, diglyme 2. Н-О, но (c) 1. LIAIH4, diethyl ether (d) 2. H-О OH H,CrO4 (e) CH3CHC=C(CH2);CH3 H2SO4, H20, acetone OH || (f) CH;ČCH,CH=CHCH,CCH3 1. LIAIH4, diethyl ether 2. H-о OH O,N || pyridine -CI (g) H3C O,N (h) + CH;COCCH3 -ОН H NO2 CH;OH (i) Cl H2SO4 НО NO2

Introductory Chemistry: A Foundation
8th Edition
ISBN:9781285199030
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Donald J. DeCoste
Chapter13: Gases
Section: Chapter Questions
Problem 137AP
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Each of the following reactions has been reported in the chemical literature. Predict the product in each case, showing stereochemistry where appropriate.

HO
H2SO4
(а) Н,С-
heat
`C,Hs
(CH3)3COOH, OsO4(cat)
(b)
(CII3);COII, IIO-
1. B,H6, diglyme
2. Н-О, но
(c)
1. LIAIH4, diethyl ether
(d)
2. H-О
OH
H,CrO4
(e) CH3CHC=C(CH2);CH3
H2SO4, H20, acetone
OH
||
(f) CH;ČCH,CH=CHCH,CCH3
1. LIAIH4, diethyl ether
2. H-о
OH
O,N
||
pyridine
-CI
(g) H3C
O,N
(h)
+ CH;COCCH3
-ОН
H
NO2
CH;OH
(i)
Cl
H2SO4
НО
NO2
Transcribed Image Text:HO H2SO4 (а) Н,С- heat `C,Hs (CH3)3COOH, OsO4(cat) (b) (CII3);COII, IIO- 1. B,H6, diglyme 2. Н-О, но (c) 1. LIAIH4, diethyl ether (d) 2. H-О OH H,CrO4 (e) CH3CHC=C(CH2);CH3 H2SO4, H20, acetone OH || (f) CH;ČCH,CH=CHCH,CCH3 1. LIAIH4, diethyl ether 2. H-о OH O,N || pyridine -CI (g) H3C O,N (h) + CH;COCCH3 -ОН H NO2 CH;OH (i) Cl H2SO4 НО NO2
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