Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 11, Problem 3LGP
Synthesize the compound shown below from methylcyclopentane and 2-methylpropane using those compounds as the source of the carbon atoms and any other reagents necessary. Synthetic tools you might need include Markovnikov or anti-Markovnikov hydration, Markovnikov or anti-Markovnikov hydrobromination, radial halogenation, elimination, and nuceleophilic substitution reactions.
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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…
Convert 2-pentanol into 2,3-dibromopentane. Draw structures of the starting material (2-pentanol) and final product
(2,3-dibromopentane), and show the two reactions needed for this synthesis. Include the structure of the intermediate
compound, and the reagents and conditions for each reaction. Then explain why 1,2-dibromopentane would not be a
significant product of this synthesis.
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…
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - Practice Problem 11.8 Show how you would prepare...Ch. 11 - Prob. 9PPCh. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - Prob. 33PCh. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Predict the products from each of the following...Ch. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 42PCh. 11 - 11.43. A synthesis of the -receptor blocker called...Ch. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - 11.46. For each of the following, write a...Ch. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Outlined below is a synthesis of the gypsy moth...Ch. 11 - Prob. 54PCh. 11 - Prob. 55PCh. 11 - Prob. 56PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...
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