Organic Chemistry As a Second Language: Second Semester Topics
4th Edition
ISBN: 9781119110651
Author: David R. Klein
Publisher: WILEY
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Question
Chapter 5.3, Problem 5.17P
Interpretation Introduction
Interpretation:
Products for the given reaction has to be predicted.
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Students have asked these similar questions
Predict the products of this organic reaction:
CH3 CH₂
||
No reaction
CH3
|
O−CH–CH2–CH3
+ KOH
A
Specifically, in the drawing area below draw the structure of the product, or products, of this reaction. (If there's more than one product, draw them in any
arrangement you like, so long as they aren't touching.)
If there aren't any products because this reaction won't happen, check the No reaction box under the drawing area.
Click anywhere to draw the first
atom of your structure.
X
Ś
Ć
Br
CH3OH
+
Br-Br
H3CO
The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the
final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product.
+Br
+ CH3OH
Br
Intermediate 1
Intermediate 2
(product)
In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction.
OH
+ Br2
+ HBr
Br
racemic mixture
• Pay attention to the reactants, they may differ from the examples. In some reactions, one part of the molecule acts as the nucleophile.
• You do not have to consider stereochemistry.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate intermediate 1 and
intermediate 2 using the → symbol from the dropdown menu.
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…
Chapter 5 Solutions
Organic Chemistry As a Second Language: Second Semester Topics
Ch. 5.1 - Prob. 5.2PCh. 5.1 - Prob. 5.3PCh. 5.1 - Prob. 5.4PCh. 5.1 - Prob. 5.5PCh. 5.1 - Prob. 5.6PCh. 5.1 - Prob. 5.7PCh. 5.2 - Propose a mechanism for each of the following...Ch. 5.2 - Propose a mechanism for each of the following...Ch. 5.2 - Propose a mechanism for each of the following...Ch. 5.3 - Prob. 5.13P
Ch. 5.3 - Prob. 5.14PCh. 5.3 - Prob. 5.15PCh. 5.3 - Prob. 5.16PCh. 5.3 - Prob. 5.17PCh. 5.3 - Prob. 5.18PCh. 5.4 - Propose a mechanism for each of the following...Ch. 5.4 - Propose a mechanism for each of the following...Ch. 5.4 - Propose a mechanism for each of the following...Ch. 5.4 - Propose a mechanism for each of the following...
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