Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 14, Problem 14.34SP
Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.
- a. 1-methoxybutane
- b. 2-ethoxy-2-methylpropane
- c. benzyl cyclopentyl ether
- d. trans-2-methoxycyclohexanol
- e. the TIPS ether of (d)
- f. cyclohexyl cyclopentyl ether
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11. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium
bromide.
a.
trans-1-bromo-3-methylcyclopentane
b. cis-1-bromo-3-methylcyclopentane
c. 1-methylcyclopentene
d. 2-methylcyclopentene
e. 3-methylcyclopentene
H3C
CH₂
?
Reagents
a.
HBr
b. Mg, ether
c. CO₂, ether then H3O+
d.
BH3, THF then H₂O₂, OH-
H3C
e.
f.
g.
h.
CH3
COOH
PBr3
NaCN then H3O+
NBS, CCl4
CrO3, H₂SO4
Select reagents from the table to show how you would carry out this transformation. If more than one route exists, use the one that requires the fewest steps; in no case will more
than 3 steps be required.
Enter your selection as a series of letters for the reagents in the order that you wish to use them, i.e. fca.
1. Which reaction conditions would be best for turning ethene into ethanol?
a.H2O, HBr
b. CH3OH, H2SO4
c.CH3OH, HBR
d. H2O, H2SO4
2. Which alkene would be non-regioselective in a reaction with HBr?
a. 2-ehyl-2-methyl-2-butene
b.2-ethyl-3-methyl-2-butene
c. 2,3-dimethyl-2-butene
d.1,2-dimethyl-2-butene
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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