Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Textbook Question
Chapter 8, Problem 18CTQ
The reactants, intermediates, final products, and all curved arrows showing bonds forming andbreaking are collectively referred to as the mechanism of a reaction. For the following reactants:
a. Explain why the original statement of Markovnikov’s rule does not help in this case, but themodern restatement of Markovnikov’s rule tells you which carbon will get the X (Cl).
b. Show the mechanism of the most likely addition reaction between the reactants.
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Item 2
Draw the organic products formed in each reaction. Consider both substitution and
elimination products, if possible. Indicate the type of reaction that happened (SN1, SN2,
E1, E2). Include stereochemistry and regiochemistry if relevant. For multiple products,
identify which is the major and which is th]e minor product.
a.
b.
C.
d.
e.
H₂C
9H
****
CH3
CH₂CH3
Br
Br
CH₂CH
C6H5
Br
-OC(CH3)3
OC(CH3)3
CH3CH₂OH
TOH
CH₂OH
Which of the following statements about an SN2 reaction is true?
A. There are two transition states.
B. There is one energy maximum.
C. The transition state can be isolated and studied.
D. For a carbon electrophile in the transition state, the hybridization of an sp3
carbon remains unchanged.
E. The reaction rate does not depend on the concentration of the electrophile.
Below is the free energy diagram for the substitution reaction of 2-chlorobutane with
hydroxide ion:
Reaction coardinate
Draw the structures, which correspond to A and C in the free-energy diagram above
for the reaction of 2-chlorobutane with hydroxide ion.
a.
b. Label the free energy of activation (AG#) and free energy change AG") on the diagram
above.
c. Is the reaction exergonic or endergonic (circle one)?
page 4 of 17
Free energy
Chapter 8 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 8 - Prob. 1CTQCh. 8 - Prob. 2CTQCh. 8 - Prob. 3CTQCh. 8 - Prob. 4CTQCh. 8 - Prob. 5CTQCh. 8 - Prob. 6CTQCh. 8 - Prob. 7CTQCh. 8 - Prob. 8CTQCh. 8 - Prob. 9CTQCh. 8 - Prob. 10CTQ
Ch. 8 - Draw the products that result from the electron...Ch. 8 - Prob. 12CTQCh. 8 - Draw the products that would result if the arrow...Ch. 8 - Prob. 14CTQCh. 8 - What information (if any) from the following...Ch. 8 - Prob. 16CTQCh. 8 - Prob. 17CTQCh. 8 - The reactants, intermediates, final products, and...Ch. 8 - Prob. 19CTQCh. 8 - Prob. 20CTQCh. 8 - Prob. 21CTQCh. 8 - Prob. 22CTQCh. 8 - Explain how you can tell from the energy diagram...Ch. 8 - Explain why the following mechanism for hydration...Ch. 8 - Prob. 25CTQCh. 8 - Prob. 26CTQCh. 8 - Prob. 27CTQCh. 8 - Prob. 28CTQCh. 8 - Prob. 29CTQCh. 8 - Prob. 30CTQCh. 8 - Prob. 31CTQCh. 8 - The hydration above is one of a family of...Ch. 8 - Prob. 33CTQCh. 8 - Which statement is false? a. A mechanistic step...Ch. 8 - Prob. 35CTQCh. 8 - Prob. 36CTQCh. 8 - Prob. 37CTQCh. 8 - Draw the complete mechanism including the...Ch. 8 - Prob. 2ECh. 8 - Explain why ethene does not react with HX ( X=Cl ,...Ch. 8 - Draw the complete mechanism of each pair of...Ch. 8 - Prob. 5ECh. 8 - Prob. 6ECh. 8 - Prob. 7ECh. 8 - Prob. 8ECh. 8 - Prob. 9ECh. 8 - Prob. 10ECh. 8 - Prob. 11ECh. 8 - Prob. 12ECh. 8 - Prob. 15ECh. 8 - A student proposes the following reaction...Ch. 8 - Prob. 17ECh. 8 - Prob. 18ECh. 8 - Prob. 19E
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