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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Using reaction free energy to predict equilibrium composition
Consider the following equilibrium:
2NO2 (g) = N2O4(g)
AGº = -5.4 kJ
Now suppose a reaction vessel is filled with 4.53 atm of dinitrogen tetroxide (N2O4) at 279. °C. Answer the following questions about this system:
Under these conditions, will the pressure of N2O4 tend to rise or fall?
Is it possible to reverse this tendency by adding NO2?
In other words, if you said the pressure of N2O4 will tend to rise, can that
be changed to a tendency to fall by adding NO2? Similarly, if you said the
pressure of N2O4 will tend to fall, can that be changed to a tendency to
'2'
rise by adding NO2?
If you said the tendency can be reversed in the second question, calculate
the minimum pressure of NO 2 needed to reverse it.
Round your answer to 2 significant digits.
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rise
☐ x10
fall
yes
no
☐ atm
G
Ar
1
Why do we analyse salt?
Curved arrows are used to illustrate the flow of electrons. Using
the provided starting and product structures, draw the curved
electron-pushing arrows for the following reaction or
mechanistic step(s).
Be sure to account for all bond-breaking and bond-making
steps.
H
H
CH3OH, H+
H
Select to Add Arrows
H°
0:0
'H
+
Q
HH
■ Select to Add Arrows
CH3OH,
H*
H.
H
CH3OH, H+
HH
■ Select to Add Arrows i
Please select a drawing or reagent from the question area
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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