Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 9, Problem 8CTQ
Interpretation Introduction
Interpretation: The product for the given reaction should be predicted.
Concept introduction:
The reaction of an
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Why do you suppose this mechanism leads to the anti-Markovnikov product? Provide a rational and discuss the potential intermediates that are involved.
The ratio between the products resulting from the reversible Diels-Alder reaction of furan and N-
phenyl maleimide can be tuned by varying the reaction temperature and solvent. Please answer
the following questions.
A) Draw the products of this reaction that agree with the product ratios at each temperature when
run either neat or in ether. Label each product as either endo or exo and be sure to indicate
stereochemistry.
Q
furan n-phenyl maleimide
+
Time
7 days
7 days
20 days
7 days
then 5 h
Temp
0 °C
ambient
ambient
0 °C
60 °C
A B
36
49
48
41
68a 23a
43
21
A
+
N-phenyl-
maleimide
(%)
14
11
ga
36
B) Draw the reaction coordinate diagram of this reaction. Label the products from part A, and
provide a drawing of any transition states.
B
The same reaction with chlorine is not much regioselective in the above. Explain the decreased regioselectivity of the following chlorination reaction by comparing the bromination reaction in the above (draw the mechanism, transition state, energy diagram, etc.). ‘Markovnikov’s or anti-Markovnikov’s rule’ is not a correct answer.
Chapter 9 Solutions
Organic Chemistry: A Guided Inquiry
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- Which substrate will result in an alkene that could be consider both the Hoffman and Saytzev product?arrow_forwardProvide specific examples/reaction scheme/mechanism for each of the following: a) Hoffman elimination b) Wittig reaction c) Zaitsev's rule d) Anti-Markovnikov's rule e) Stereoelectronic effectarrow_forwardFrom the below reactions, indicate which product is the Markovnikov product and which product is the anti-Markovnikov product?arrow_forward
- Given three equally branched structures and with only a difference in the type of group attached to each (OH, NH3, or OTs), which compound would react faster in an SN1 reaction?arrow_forwardWhich reaction or statement regarding nucleophilic substitutions is incorrect? A) C₁ + 2 H2O ноттон + 2 HCI B) ta CI+MeOH to + HCI C) D) The rate-limiting step in SN1 reactions is the initial step, loss of the leaving group. Nucleophilic substitution reactions that follow second-order kinetics involve complete inversion of configuration.arrow_forwardFor the given molecule, highlight any nucleophilic sites in red and any electrophilic sites in blue. O: 439 0-Harrow_forward
- How do you properly write an SN1 reaction, with transition states/intermediate steps included?arrow_forwardAccording to the LUMO density map, on which face is the LUMO electronically more exposed to nucleophiles? Based on this data, which face would be more electronically favored? (These questions go hand in hand.)arrow_forwardFor the reagent sequence shown, what is the expected major product?arrow_forward
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