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Pushing Electrons

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter3: Mechanisms

Section: Chapter Questions

Problem 93EQ

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Which reaction is the fastest, which is the slowest? I want to check my work and see if I am correct

4. In the preparation of TNT, which reaction is the fastest? Which is the slowest?
Kest
EDG
HNO3
NO,
O2N.
NO2 0
HNO3
H2SO4
HNO3 do ooten o
H2SO4
H2SO4
othro/Para NObuest
Eirector
woled noilase dose tol loubo
fastest
5. Some electrophilic aromatic substitutions are reversible. What are the products of
each of the following reactions? Also, provide mechanisms.
SO3H H2O*

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Below is the equation for a nucleophilic substitution reaction and some experimental data. CH3CH2Br + CH3COO- ⇌ CH3CH2CO2CH3 + Br- Rate = k [CH3CH2Br][CH3COO-] Which mechanism would best fit the data?
Which compounds from 5a-d will react with hydroxide in the fashion shown. Which reaction will be the fastest and slowest? Explain using knowledge of carbonyl chemistry, pka and leaving groups.
In SN2 reactions of haloalkanes, the order of reactivity is RI>RBr>RCl>RF. Alkyl iodides are considerably more reactive than alkyl fluorides, often by factors as great as 106. All 1-halo-2,4-dinitrobenzenes, however, react at approximately the same rate in nucleophilic aromatic substitutions. Account for this difference in relative reactivities.
What steps are needed to prepare phenylacetylene, C6H5C = CH, from each compound: (a) C6H5CH2CHBr2; (b) C6H5CHBrCH3; (c) C6H5CH2CH2OH?
Predict the major organic product formed when the compound shown below undergoes a reaction with H2O2 and then is heated in H20. I understand that it's a cope elimination so I know how it goes from an amine to an amine oxide, but I haven't done this type of problem with a heterocycle before, so the 2nd step confuses me. Any help would be greatly appreciated.
(a) What happens when CH3—O—CH<sub3 is heated with HI?(b) Explain mechanism for hydration of acid catalyzed ethene :CH2 = CH2 + HzO CH3—CH,—OH
There are two isomeric cyclohexa-1,4-diene products when benzoic acid undergoes the Birch reduction (see Problem 25.24). (a) Draw the mechanism that leads tothe formation of the major product. (b) Will the Birchreduction of benzoic acid occur faster or slower than theBirch reduction of benzene itself? Hint: Is –CO2H anelectron-donating or an electron-withdrawing group?
Match the questions with the correct descriptions below: Sn2, E2 E1cb Sn1, E1 (anti) E2, E1cb Sn1, E1 2 steps poor leaving group 2 carbons removed from a carbonyl group carbanion intermediate 3°>allylic, benzylic>2°>1°>CH₃ carbocation intermediate Ist order reaction (r=k[RX]) H-X anti no intermediate 2nd order reaction (r=k[RX][Nu]) polar aprotic solvent
Indicate the complete mechanisms for each step of the synthesis below.
What products will be obtained from the E1 reaction of the alkyl halides in Problem 45?
For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent. (d) Sodium cyanide in dimethyl sulfoxide (e) Sodium azide in aqueous ethanol (f) Sodium hydrogen sulfide in ethanol
Rank the following in increasing order of reactivity towards nucleophilic acyl substitutiona. CH3COCl, CH3COOCH3, CH3CONH2b. CH3COOCH3, CH3COOCH2CCl3, CH3COOCH(CF)3

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