Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 8.6, Problem 8P
Instead of the three-step process of Mechanism 8.3, the following two-step mechanism might be considered:
1. 
2. 
This mechanism cannot be correct! What is its fundamental flaw?
Mechanism 8.3
Acid-catalyzed Hydration of
The Overall Reaction
The Mechanism:
Step 1: Protonation of the carbon–carbon double bond in the direction that leads to the more stable carbocation:
Step 2: Water acts as a nucleophile to capture
Step 3: Deprotonation of
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8. Consider the nucleophilic substitution reaction below:
CI:
+ CH3OH
step 1
intermediate A
CH3OH
step 2
H
CH3
Draw the mechanism by using the curved arrow notation on the above reaction, to indicate the
electron movement for both the formation of the intermediate A and for the product. You will
need to draw Intermediate A and include the side product (s). Please show electron pairs and
charges
Step 4a: Classify step.
The target product is present, but the reaction is not over. The ethoxide ion has been regenerated.
:0:
:0:
What is the key process in the next step of the mechanism?
proton transfer
formation of a o bond between nucleophile and electrophile
loss of a leaving group
carbocation rearrangement (e.g., methyl or hydride shift)
(dehydrobromination)
A chemist carried out an elimination reaction
of 1,1-dimethyl-2-
bromocyclopentane. The chemist expected the
reaction to yield alkene Z as product. However,
alkene Z DID NOT form. Instead, three alkenes
were produced: one alkene was the major
product, the other two alkenes was the minor
products.
What was the major alkene product that
formed?
Br
Select one:
A. I
B. II
C. IV
D. III
alcohol
HEAT
||
Z
=
+
(HBr)
IV
Chapter 8 Solutions
Organic Chemistry - Standalone book
Ch. 8.1 - What three alkenes yield 2-methylbutane on...Ch. 8.2 - Prob. 2PCh. 8.2 - Prob. 3PCh. 8.3 - Prob. 4PCh. 8.4 - Prob. 5PCh. 8.4 - Give a structural formula for the carbocation...Ch. 8.5 - Prob. 7PCh. 8.6 - Instead of the three-step process of Mechanism...Ch. 8.6 - The rates of hydration of the two alkenes shown...Ch. 8.6 - Is the electrophilic addition of hydrogen chloride...
Ch. 8.7 - You can calculate the equilibrium constant for the...Ch. 8.7 - Does the presence or absence of a catalyst such as...Ch. 8.7 - The gas phase reaction of ethanol with hydrogen...Ch. 8.8 - Prob. 14PCh. 8.8 - Hydroborationoxidation of -pinene, like its...Ch. 8.10 - Arrange the compounds 2-methyl-1-butene,...Ch. 8.10 - Give the structure of the product formed when each...Ch. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.12 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.13 - Prob. 22PCh. 8.14 - Prob. 23PCh. 8.14 - Prob. 24PCh. 8 - How many alkenes yield...Ch. 8 - Prob. 26PCh. 8 - Catalytic hydrogenation of...Ch. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - A single epoxide was isolated in 7984% yield in...Ch. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - On catalytic hydrogenation over a rhodium...Ch. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - 1-Butene has a higher heat of hydrogenation than...Ch. 8 - Match the following alkenes with the appropriate...Ch. 8 - The heats of reaction were measured for addition...Ch. 8 - Complete the following table by adding + and -...Ch. 8 - Match the heats of hydrogenation (107 kJ/mol,...Ch. 8 - The iodination of ethylene at 25 C is...Ch. 8 - Specify reagents suitable for converting...Ch. 8 - (a) Which primary alcohol of molecular formula...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Prob. 50PCh. 8 - On being heated with a solution of sodium ethoxide...Ch. 8 - Compound A (C7H15Br) is not a primary alkyl...Ch. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - A mixture of three alkenes (A, B, and C) was...Ch. 8 - Reaction of 3,3-dimethyl-1-butene with hydrogen...Ch. 8 - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol...Ch. 8 - Prob. 58PCh. 8 - East Indian sandalwood oil contains a hydrocarbon...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - On the basis of the mechanism of acid-catalyzed...Ch. 8 - As a method for the preparation of alkenes, a...Ch. 8 - Which of the following is the most reasonable...Ch. 8 - Prob. 68PCh. 8 - Oxymercuration Concerns about mercurys toxicity...Ch. 8 - Prob. 70DSPCh. 8 - Prob. 71DSPCh. 8 - Prob. 72DSPCh. 8 - Prob. 73DSPCh. 8 - Oxymercuration Concerns about mercurys toxicity...
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