Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 17, Problem 17.51AP
Interpretation Introduction
(a)
Interpretation:
A curved-arrow mechanism for the cyclization of
Concept introduction:
A
The nucleophilic substitution reactions are the reactions in which one nucleophile attacks the electrophilic center and eliminates another group in the compound. These reactions depend upon the nucleophilicity and concentration of the nucleophile.
The
Interpretation Introduction
(b)
Interpretation:
A curved-arrow mechanism for the cyclization of
Concept introduction:
A chemical reaction in organic chemistry which is used for the synthesis of cyclopentenones is known as cyclization reaction.
The nucleophilic substitution reactions are the reactions in which one nucleophile attacks the electrophilic centre and eliminates another group in the compound. These reactions depend upon the nucleophilicity and concentration of the nucleophile.
The
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Students have asked these similar questions
(i)
Explain why a high reaction temperature favours elimination reactions, instead of
substitution reactions.
(ii)
Explain why polar aprotic solvents favour Sn2 reaction but not favour SN1 reaction.
1. The acid catalyzed synthesis of diethyl ether occurs via and SN2 reaction although a protic
solvent is used. Discuss in your group why this substitution cannot occur via an SN1 reaction, and
why E1 and E2 reactions do not occur. Your answer should be in complete sentences and use
appropriate vocabulary to describe the molecules involved.
2
H,SO,(aq)
+ H2O
ОН
The natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish
this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem
Comm. 2014, 50, 13725)
(a) Using three molar equivalents of BrCL please provide a mechanism to account for the formation of the bracketed structure (you do
not need to show stereochemistry in this mechanism)
HB
(3 equiv)
myrcene
balomon
8.61a
Add curved arrow(s) to show the mechanism steps.
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Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Prob. 17.1PCh. 17 - Prob. 17.2PCh. 17 - Prob. 17.3PCh. 17 - Prob. 17.4PCh. 17 - Prob. 17.5PCh. 17 - Prob. 17.6PCh. 17 - Prob. 17.7PCh. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Prob. 17.14PCh. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22APCh. 17 - Prob. 17.23APCh. 17 - Prob. 17.24APCh. 17 - Prob. 17.25APCh. 17 - Prob. 17.26APCh. 17 - Prob. 17.27APCh. 17 - Prob. 17.28APCh. 17 - Prob. 17.29APCh. 17 - Prob. 17.30APCh. 17 - Prob. 17.31APCh. 17 - Prob. 17.32APCh. 17 - Prob. 17.33APCh. 17 - Prob. 17.35APCh. 17 - Prob. 17.36APCh. 17 - Prob. 17.37APCh. 17 - Prob. 17.38APCh. 17 - Prob. 17.39APCh. 17 - Prob. 17.40APCh. 17 - Prob. 17.41APCh. 17 - Prob. 17.42APCh. 17 - Prob. 17.43APCh. 17 - Prob. 17.44APCh. 17 - Prob. 17.45APCh. 17 - Prob. 17.46APCh. 17 - Prob. 17.47APCh. 17 - Prob. 17.48APCh. 17 - Prob. 17.49APCh. 17 - Prob. 17.50APCh. 17 - Prob. 17.51APCh. 17 - Prob. 17.52APCh. 17 - Prob. 17.53APCh. 17 - Prob. 17.54APCh. 17 - Prob. 17.55APCh. 17 - Prob. 17.56APCh. 17 - Prob. 17.57APCh. 17 - Prob. 17.58APCh. 17 - Prob. 17.59AP
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- A student was given from the list of the conmpounds below A, B and D blindly and asked to identify them all. He treated each of them with Brady's reagent (2,4-ditrophenylhydrazine) and isolated a bright yellow compound for one of them, but the other two gave false negatives. The student reasoned that the false negatives may be due to sterics and, on further thinking, it dawned on him that he might be able to rule out one of the false negatives with the haloform test. What compound did he find compatible with the haloform test? That compound did indeed give a false negative in the Brady test. Which of the other two was positive in the Brady test? A = haloform B = Brady A = haloform D = Brady B = haloform A = Brady B = haloform D = Brady D = haloform A = Brady D = haloform B = Bradyarrow_forwardGive the reagents suitable for effecting each of the following reactions, and write the principal products. If an ortho, para mixture is expected, show both. If the meta isomer is the expected major product, wrote only that isomer. Nitration of benzene Nitration of the product of (a) Bromination of toluene Bromination of (trifluoromethyl)benzene Sulfonation of anisole Sulfonation of acetanilide (C6H5NHCOCH3) Chlorination of bromobenzene Friedel-Crafts alkylation of anisole with benzyl chloride Friedel-Crafts acylation of benzene with benzoyl chloride Nitration of the product of (i) Clemmensen reduction of product from (i) Wolff-Kishner reduction of product from (i)arrow_forward(a) Given and Scara were given a task of synthesising (2-methylprop-1- enyl)cyclohexane 2 (A potential TB drug). After a brief discussion with each other, Given proposed Method A to synthesise 2 from cyclohexanecarbaldehyde 1 while Scara proposed Method B that started from hydroxymethylcyclohexane 3. When designing a synthetic route for drug molecule, you have to make sure the synthetic process is as efficient as possible (e.g. few synthetic steps, mostly making one product and more). THF A Ph Ph Ph B 3 1. PCC 2. isopropyl magnesium vromide 3. H₂SO4 100 °C OH Method B is not preferred synthetic route due to the number of steps involve (3 steps vs 1 step for Method A). What else is making method A unfavorable synthetic method? Use curly arrows to explain this effect. (Ctrl) -arrow_forward
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