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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 3CTQ

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Tag the carbons in this molecule that are bonded to the H atoms that could be most easily abstracted by a radical reaction step. That is, find and
tag the carbons with the C-H bonds that are the most easily cleaved homolytically.
X
D
C

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The following molecules are subject to substitution (SN1 or SN2) reaction conditions. a) Identify if the leaving group (-Br) is attached to a 3°, 2°, 1°, or methyl Carbon. b) Rank the molecule with respect to their SN1 reactivity, with 1 being the fastest and 4 being the slowest. c) Rank the molecule with respect to their SN2 reactivity, with 1 being the fastest and 4 being the slowest. Br Br CH3B Br a. type of Carbon on C-Br b. SN1 reactivity (1 fastest, 4 slowest) c. SN2 reactivity (1 fastest, 4 slowest)
H₂C H H₁C Br NBS CH, CH₂ CC, hv **You may assume that Br-Br is formed by a side reaction that occurs (which we discussed in class). This is useful for one of the steps of the mechanism.
Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. LOCH3 LOCH3 HNO3 / CH3CO₂H O₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. ● In cases where there is more than one answer, just draw one.
Fill both dashes in the paragraph Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is: ---------.
Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. OH CCI3 H2SO4 CCI3 CI- First stage in synthesis of the insecticide DDT, which is now banned in the US You do not have to consider stereochemistry. Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one.
Draw a curved arrow mechanism for the substitution reaction that will occur with the alkyl halide and nucleophile below, adding steps as necessary. Be sure to include all nonbonding electrons and all nonzero formal charges, and show all species that react or are formed in this reaction.
Give the curved arrow mechanism showing the homolysis of the appropriate C–H bond by reaction with a Br• radical. Draw curved arrows to show C–H bond homolysis. Add or remove any bonds needed.
For the given molecule, highlight any nucleophilic sites in red and any electrophilic sites in blue. O: 439 0-H
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× Your answer is incorrect. 1) RCO₂H ? 2) [H2SO4], OH Modify the given structure to draw the major product(s). Use the single bond tool to interconvert between double and single bonds. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and Paste to save drawing time. H3C H3C CH3 CH3 OH H3C CH3 O OH HO CH3 Edit Drawing CH3 SUPPOR
Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction.

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