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
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
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
pt
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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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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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- 1. MgBr 1. Dry ether OH 2. Hао 2. Br AIB 3 AIBra d = Electrophilic addition g = SN1 Nucleophilic a = Proton transfer substitution h = SN2 Nucleophilic b = Lewis acid/base e = El Elimination substitution c = Radical chain f= E2 Elimination substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - i for your answers. 1. 2. Submit Answer Retry Entire Group 8 more group attempts remainingarrow_forwardQ10. For each of the following reactions (a-b), predict whether the substitution is more likely to occur following an Sn1 or Sn2 mechanism; explain your reasoning. Draw the products of each nucleophilic substitution paying particular attention to the stereochemistry of carbon 1. a) Br, CH3 MeOH H3C b) Br NaOH 1 DMF* H3C *N,N-dimethylformamidearrow_forward1. What is the function of CH»Ch in the bromination reactions? Why can it fulfil this role? 2. In not more than three (3) sentences, explain why terminal alkynes are acidic. 3. What impurities are removed when acetylene gas is made to pass through an acidified solution of CuSO:? 4. Explain the difference in the rate of free radical bromination reactions of toluene and cyclohexane. 5. Give the reagent er chemical cempounde, Previde only Ehe reasents nu Would differentiate tefelarrow_forward
- 17. a. Label the reactive features, highlight the most reactive one, then highlight what it needs. Also, state if the reaction will start to create a carbocation, carbon radical, or carbanion, or will cause loss of aromatic character. If a carbocation, carbon radical, or carbanion starts to develop, label where that will occur. CH3 with Cl, and FeCl, CH2 CH3 b. Use mechanism arrows to illustrate the reaction that occurs. c. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance-stabilized intermediate. d. Continue labeling and diagramming the reaction until you find the major stable product(s). e. Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.arrow_forwardThe following compounds are major products of an elimination reaction with an alkyl halide. Determine the structure of the alkyl halide. (P.S. write the overall reaction mechanism). Tip: Remember your Markovnikov’s rule. Follow the progress of the reaction and look at the stability of the intermediate products and transition states to determine the minor and major products. ANSWER ONLY THE FIRST 3 LETTERS.arrow_forwardPart 3. Predict the SN2/Radical Product. Predict the major organic product for each of the following reactions. Be sure to show stereochemistry when appropriate. MeO h 14 ** NaSCH3 NBS/hv/CCI4 NaN3arrow_forward
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