Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 11, Problem 11.49SP
Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.
- a. PBr3
- b. SOCl2
- c. Lucas reagent
- d. concentrated HBr
- e. TsCl/pyridine, then NaBr
Expert Solution & Answer
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Students have asked these similar questions
From the table of reagents shown below, show how you synthesize the product from the given reactant.
OCH₂CH3
OH
a. NBS, (PhCO₂)2
b. Br2, FeBr3
c. Br₂, H+
d. OH
e. NaOH(s), A
f. HNO3, H₂SO4
g. H₂ CrO4
Reagents available
h. CH3 CI, AICI,
o. CuCN
i. CH3 CH₂ Br
p. H₂O+, A
j. CH₂O, A
q. CH3 CH₂ COCI, AICI,
k. CH3COCI, AICI3
r. H₂NNH₂, OH, A
1. Mg, Et₂ O
s. H₂, Pd/C
m. CO₂ (s) then H3O+ t. H₂PO₂
n. HONO 0°C
u. Cl₂, FeCl3
(Enter the letter(s) of the reagent(s) needed in the box, in the order that they must be used. No more than two steps are required
to perform the synthesis. Note that a retrosynthetic arrow is used, and therefore the reactant is shown on the right.)
Answer:
Identify the missing reagent(s), reactant(s) or final product(s). Some transformations
may require more than one step.
A.
B.
C.
MeO₂C
CO₂Me
Br₂, H₂O
70 °C
CN
CN
Br
?
Br
D.
E.
in
?
?
LIAIH
Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter "none"
for step 3.
r
Alcohol Starting Materials
1. methanol
2. ethanol
3. 1-propanol
4. 2-propanol
5. cyclohexanol
Reagents available
a. LiAlH₁ f. PBr3
b. H₂SO4
c. HCI
d. HBr
i. CH3 MgBr; then H3O+
e. SOC1₂ j. CH3 CH₂ MgBr; then H3O+
g. CrO3, H₂ SO4, H₂O
h. NaH
k. CH3 CH₂ CH₂ MgBr; then H3O+
I. C6H5 MgBr (phenylmagnesium bromide); then H3O+
m. (CH3)2 CHMgBr: then H3O+t
n. Dess-Martin periodinane (DMP)
Write the number/letters of the alchol/reagents in the boxes below.
Alcohol starting material
Reagent for step 1
Reagent for step 2
Reagent for step 3
Chapter 11 Solutions
Organic Chemistry (9th Edition)
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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