ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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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
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12. Which reagents/conditions would lead to the transformation depicted below in high yield?
a. NaOMe, MeOH
b.
MeOH, H₂O*
c. NaOEt, EtOH
13. In the structure of 2-fluoropropanoic acid shown, the oxidation
number on C1 is
the oxidation number on C2 is
a. +1, +2, -3
b. -3, +1, +3
d. NaOH, H₂O
e. two of these
, and the oxidation number on C3 is,
c. 0, 0, 0
d. +3,0,-3
e.
+2,0, -2
???
OH
14. What will be the outcome of the following reaction sequence?
B.
1. NaOEt, EtOH
2. PCC
3. isopropylMgBr
4. H₂0¹
???
a.
2-ethyl-3-isopropyl-2,3-dimethyloxirane
b. 2,3,4-trimethyl-3,4-epoxyhexane
c. 1,2,3,4-tetramethyl-2,3-epoxypentane
d. Both a and b are suitable.
e. All of the above are correct.
OH
15. What is a suitable IUPAC name for the structure shown at the
right?
OH
D.
F
H
OH
LOH
CH3
3
OH
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
Provide the principle organic product for the following reactions. If more than one product is formed indicate which one you expect to be the major product.
Chapter 11 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
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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