4 pts total)re is Aromatic (A),(circle one)A AANion with Cl₂/FeCls. (6 pts)acids shown to right) (6 pts)al31. Consider the Friedel-Crafts (FC) alkylation of N-phenylacetamide (shown below) in which reaction with1-chloropropane and AlCl3 produces two isomers of isopropyl N-phenylacetamide. (20 pts)1. Draw the complete reaction mechanism for the formation of the ortho product (para is also formed) (10 pts)2. Is this reaction faster or slower than the similar FC reaction starting with benzene (C6H6)? Explain why. (4 pts)3. Explain why this reaction produces the ortho and para products (but not meta). (6 pts)Use your mechanism to help explain parts #2 and #3. Use additional drawings and words as needed.toAICIN-phenylacetamide455staAHO O00 10HСОИН08HНИMOHO HOHO10

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Answered: 4 pts total) re is Aromatic (A),…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

4 pts total)
re is Aromatic (A),
(circle one)
A AAN
ion with Cl₂/FeCls. (6 pts)
acids shown to right) (6 pts)
al
3
1. Consider the Friedel-Crafts (FC) alkylation of N-phenylacetamide (shown below) in which reaction with
1-chloropropane and AlCl3 produces two isomers of isopropyl N-phenylacetamide. (20 pts)
1. Draw the complete reaction mechanism for the formation of the ortho product (para is also formed) (10 pts)
2. Is this reaction faster or slower than the similar FC reaction starting with benzene (C6H6)? Explain why. (4 pts)
3. Explain why this reaction produces the ortho and para products (but not meta). (6 pts)
Use your mechanism to help explain parts #2 and #3. Use additional drawings and words as needed.
to
AICI
N-phenylacetamide
455
sta
AHO O
00 10H
СОИН
08H
НИ
MOHO HO
HO
10

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Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure via resonance. For the reaction below, draw the structure of the stabilized reaction intermediate in the box below. CI F3C CF3 NO₂ F3C N CF3 NO₂ • You do not have to consider stereochemistry. • Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than one resonance structure is possible, only draw the most important one.
2. a) Provide the missing reaction product(s), or conditions to the following reactions. ACO + hv DCM, -55 °C NaOH (aq) C11 H1602
Which mechanism is consistent with the reaction below? (CH3)3CBr+OH-→(CH3)3COH+Br- 1. (CH3)3CBr+(CH3)3COH→2(CH3)3C++ OH- + Br-2. (CH3)3CC(CH3)3+BrOH→(CH3)3COH+ Br- 1. (CH3)3CBr→(CH3)3C++Br-2. (CH3)3C++OH- →(CH3)3COH 1. (CH3)3CBr+(CH3)3COH+OH- + Br- →(CH3)3CC(CH3)3+2BrOH2. (CH3)3CC(CH3)3+2BrOH→(CH3)3COH+Br- 1. (CH3)3COH+ OH- →(CH3)3C++H2O+O2- 2. (CH3)3C++HBr+O2-→(CH3)3COH+Br-
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III. Which alkyl halide in each of the following pairs will react faster in an SN2 reaction with OH? Explain your answer briefly.- (a) Bromobenzene or benzyl bromide, C6H5CH2Br (b) CH3CI or (CH3)3CCI (c) CH3CH=CHBR or H2C=CHCH2BR
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(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) Ph THF A Ph Ph B H₂SO4 100 °C 3 OH (iii) In analysing both these methods, are there other possible alkene products other than methylenecyclohexane 2? Use mechanistic details to support your answer.
. (a) Azulene, shown below, has the ability to react with both electrophiles as well as nucleophiles. Use resonance to show how this is possible, indicating in the IUPAC numbering system which C's will react in which way. (b) Hence, write down the product of reaction between azulene and (i) AICI3/CH3COCI. (ii) K* OMe/MeOH. c. What products would you expect from each of the reactions in (b) above if azulene were substituted as follows:
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7. For each pair of compounds, say which compound is the best SN2 substrate.(a) 2-methyl-1-iodopropane or tert-butyl iodide(b) cyclohexyl bromide or 1-bromo-1-methylcyclohexane(c) 2-bromobutane or isopropyl bromide(d) 1-chloro-2,2-dimethylbutane or 2-chlorobutane(e) 1-iodobutane or 2-iodopropane

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