ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 10, Problem 14PP
Practice Problem 10.14
Show how the following compounds could be synthesized from phenylacetylene
(a) 1-phenylpropyne,
(b) 1-phenyl-1-butyne,
(c)(Z)-1-phenylpropene, and
(d)(E)-1-phenylpropene.
Begin each synthesis by writing a retrosynthetic analysis.
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Practice Problem 13.36b
Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the
following epoxide from acetylene:
H"
'Et
The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters
(without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer.
A
B
C
D
DMP or PCC
На, Pt
EtBr
PHCH2BR
E
F
H
H2SO4, H20, HgSO4
МСРВА (RCO3зН)
Na, NH3 (/)
H2, Lindlar's cat.
I
K
TSCI, py
PhBr
NANH2
1) EtMgBr; 2) H30+
Consider an E2 reaction between (2-bromoethyl)cyclohexane and base
potassium tert-butoxide. Describe the rate of elimination when each of the
following changes occurred:
(i) The base is changed to sodium hydroxide.
(ii) The halogen atom of alkyl halide is replaced by chlorine.
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your
answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
OH
(c) ethylene oxide
(a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Br
OH
+
(9) H₂ SO4 (anhydrous) Na, NH3 (1)
(k) NBS, heat
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate) PBr3
(PCC)
(h) NaOH
(N-bromosuccinimide)
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Chapter 10 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - Synthesize each of die following compounds by...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 36PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 38PCh. 10 - Prob. 39PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - 10.41 Hydrogen peroxide and ferrous sulfate react...Ch. 10 - Prob. 42PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...
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