Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 12, Problem 12.24SP
covered a synthesis of
- a. Do the spectra confirm the right product? If not, what is it?
- b. Explain the important peaks in the IR spectrum.
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4. Circle the electrophilic and nucleophilic atoms in each substitution reaction below.
Provide the neutral organic product; where a stereocenter is created, use a wavy bond
to indicate a mixture of configurations or wedges/dashes for stereospecific reactions.
Also, provide the dominant reaction mechanism (Sn2 or SN1) somewhere in each box.
A.
Br
NaSEt
DMF
В.
ELOH
C.
.SO2NHNA
Cl
+
D.
NaH
Br-
HO,
DMF
One of the steps in the mechanism of the above reaction as shown below. Draw the structure of all the products of this
reaction.
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1
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Eto
O
Eto
O
3. NaOH, H₂O, heat
4. HCI, H₂O, heat
One of the steps in the mechanism of the above reaction is shown below. Draw the structure of all of the products of this reaction.
O
OEt
O
1. Eto Na
2 Å
OH
You do not have to consider stereochemistry.
• Draw enolate anions in their carbanion form.
. You should include all products.
Ôno P
Ć
[References)
. Include counter-ions, e.g., Na, I, in your submission, but draw them in their own separate sketcher.
. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
. Separate multiple products using the + sign from the drop-down menu.
///-000- IF
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8.
h.
OH
HCI (excess)
TSO
H₂SO4
A
Part IV. Predict the product X. Draw the complete, detailed mechanism (curved arrows) to show how the
tosylate will be eliminated to form molecule X and how molecule X will undergo an addition reaction to
form the final halohydrin-like products, using mechanistic skills gained in this course.
H₂O
150 °C
X
Br₂
LOH
Br
ibni
+
Br
Q₂H HOM S
Chapter 12 Solutions
Organic Chemistry (9th Edition)
Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6PCh. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...
Ch. 12.15C - Prob. 12.11PCh. 12 - Prob. 12.12SPCh. 12 - Prob. 12.13SPCh. 12 - All of the following compounds absorb infrared...Ch. 12 - Prob. 12.15SPCh. 12 - Four infrared spectra are shown, corresponding to...Ch. 12 - Predict the masses and the structures of the most...Ch. 12 - Prob. 12.18SPCh. 12 - Prob. 12.19SPCh. 12 - (A true story) While organizing the undergraduate...Ch. 12 - Prob. 12.21SPCh. 12 - Prob. 12.22SPCh. 12 - An unknown, foul-smelling hydrocarbon gives the...Ch. 12 - covered a synthesis of alkynes by a double...Ch. 12 - Three IR spectra are shown, corresponding to three...Ch. 12 - Prob. 12.26SPCh. 12 - Prob. 12.27SPCh. 12 - Prob. 12.28SPCh. 12 - The ultimate test of fluency in MS and IR is...Ch. 12 - Prob. 12.30SPCh. 12 - Consider the following four structures, followed...
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