Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 20, Problem 5Q
Select the stronger base from each pair (in aqueous solution):
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The Concept of Aromaticity
21.15 State the number of 2p orbital electrons in each molecule or ion.
(a)
(b)
(e)
(f)
(c)
(d)
(h)
(i)
DA
(k)
21.16 Which of the molecules and ions given in Problem 21.15 are aromatic according to the
Hückel criteria? Which, if planar, would be antiaromatic?
21.17 Which of the following structures are considered aromatic according to the Hückel
criteria?
---0-0
(a)
(b)
(c)
(d)
(e)
(h)
H
-H
.8.0-
21.18 Which of the molecules and ions from Problem 21.17 have electrons donated by a
heteroatom?
1. Show the steps necessary to make 2-methyl-4-nonene using a
Wittig reaction. Start with triphenylphosphine and an alkyl
halide. After that you may use any other organic or inorganic
reagents.
2. Write in the product of this reaction:
CH3
CH₂
(C6H5)₂CuLi
H₂O+
3. Name this compound properly, including stereochemistry.
H₂C
H3C
CH3
OH
4. Show the step(s) necessary to transform the compound on the
left into the acid on the right.
Bri
CH2
5. Write in the product of this
LiAlH4
Br
H₂C
OH
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Prob. 3PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 5PPCh. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Practice Problem 20.11 In the preceding examples...
Ch. 20 - Prob. 11PPCh. 20 - Prob. 12PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 14PPCh. 20 - Prob. 15PPCh. 20 - PRACTICE PROBLEM
20.16
An amine A has the...Ch. 20 - PRACTICE PROBLEM Sulfonamides of primary amines...Ch. 20 - PRACTICE PROBLEM
20.18 (a) Starting with aniline...Ch. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - Prob. 28PCh. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - 20.34 Using reactions that we have studied in this...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W:
Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 51PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 54PCh. 20 - Which of the following would be soluble in dilute...Ch. 20 - Which would yield propylamine? (d) Two of the...Ch. 20 - Select the reagent from the list below that could...Ch. 20 - Prob. 4QCh. 20 - 20.5 Select the stronger base from each pair (in...
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