Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 18, Problem 2Q
Interpretation Introduction
Interpretation: The missing reagents and intermediates, in the given synthesis, are to be provided.
Concept introduction:
The compound formed by the reaction of an
Enamines are good nucleophiles that are alkylated, as well as acylated.
The alkylation of enamines goes through
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Consider the reaction conditions provided in the question(s) below question.
Determine the type of reaction that will occur.
Identify the role of potassium tert-butoxide in this reaction.
Br
KOtBu
tBuOH
A) strong base
B) weak base or nucleophile
C) electrophile
D) solvent
Alcohols are acidic in nature. Therefore, a strong base can
abstract the acidic hydrogen atom of the alcohol in a process
known as deprotonation. The alcohol forms an alkoxide ion by
losing the proton attached to the oxygen atom of the hydroxyl (
-OH) group. The alkoxide formed can act as a base or a
nucleophile depending on the substrate and reaction conditions.
However, not all bases can abstract the acidic proton of alcohols
and not all alcohols easily lose the proton. Deprotonation
depends on the strength of the base and the acidity of the
alcohol. Strong bases, such as NaNH2, can easily abstract a
proton from almost all alcohols. Likewise, more acidic alcohols
lose a proton more easily.
Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol.
Check all that apply.
► View Available Hint(s)
CH3CH,OH + NH3 →CH,CH,O-NH
CH3
CH3
H3C-C-H+NH3 → H3 C-C-H
OH
O-NH
CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3
CHC12
Cl₂…
Write a synthesis to convert ethane to the following compound shown below. Note: the
synthesis has to be conducted in a basic medium throughout. No acidic conditions
allowed.
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...Ch. 18 - Prob. 1QCh. 18 - Prob. 2QCh. 18 - Prob. 3QCh. 18 - Prob. 4QCh. 18 - Prob. 5Q
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- Alcohols are very useful organic compounds because there are many ways to synthesize larger and more complex molecules starting with simple alcohols. The reactions you will examine form a strong basis for synthetic tools that an organic chemist would use. You will be expected to predict the major products of reactions under the conditions given. The key to doing this is to look carefully at the conditions and remember how those conditions affect the products. It is a good idea to have an index card file of the reactions as you learn them. Dehydration (loss of water) - There are two forms of dehydration reactions with alcohols - ether formation and elimination (alkene formation). In both reactions you are looking for the components of water (OH and H) that will be removed in the reaction. Ether Formation - Two alcohols will form an ether link by loss of water forming an ether product with an acidic catalyst (typically H2SO4) at 140\deg C. One alcohol loses the hydroxyl group and one…arrow_forwardwhat will be the type of interaction of ethane with bromine: a) radicals b) ionic c) nucleophilic d) electrophilicarrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction.arrow_forward
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