Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 10, Problem 6PP
Interpretation Introduction
Interpretation:
The percentage of the products formed by the chlorination of the given reactants is to be determined. Also, the reactivity order of hydrogen atoms is to be compared.
Concept introduction:
The product percentage of the compounds is calculated by the formula:
The reactivity and product percentage vary directly. The hydrogen atoms that are more reactive will convert easily into products and will give more yields.
However, the actually yield and theoretical yield do not always match. They may vary and the exact trend for the reactivity is on the basis of the actual yield and not the theoretical yield.
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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+
13.34 Draw structures for the following compounds. When necessary, show stereochemistry
by the use of appropriate conventions.
(a) 1-chloro-1-ethoxyethene
(c) 1,3-dichloro-2-propanol
(e) (R)-3-methyl-5-hexen-3-ol
(g) (S)-3-methyl-1-pentyn-3-ol
(i) (R)-5,5-đimethyl-3-heptanol
(b) (E)-1-methoxy-2-propoxyethene
(d) cyclobutylmethanol
(f) (S)-2-chloro-1-propanol
(h) 2-nitroethanol
G) (3S,4R)-4-methyl-3-hexanol
The following two sets of reactions [(a) and (b)] show possibilities for arrow
pushing in individual reaction steps. Identify which is wrong and explain why.
Then using the correct arrow pushing, label which molecule is the nucleophile
and which is the electrophile.
(b)
H3C
(a)
i-CH3 + :F
H3C
C-CI:
H3C--Ci:
C-CH3
H3C
H3C
H3C
..
H3C-CI
:I-CHg + :Cl:
:Cl:
H3C
H3C
1.
C-CH3
C-C1:
H3C
H3C
..
H3C
Chapter 10 Solutions
Organic Chemistry
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 - 10.32 Synthesize each of the following compounds...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 35PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - Prob. 37PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 39PCh. 10 - Prob. 40PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...Ch. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - 10.2 In the radical chlorination of methane, one...Ch. 10 - Prob. 3QCh. 10 - Use the single-bond dissociation energies of Table...Ch. 10 - Prob. 5QCh. 10 - Prob. 6Q
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