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문제 4
Show the mechanism for the generation of the acylium ion if an acid anhydride is used instead of an acyl chloride for the source of the acylium ion.
문제 5e,f
What is the major product of a Friedel–Crafts alkylation using the following alkyl chlorides?
e. (CH3)2CHCH2Cl
f. CH2=CHCH2Cl
문제 10c
Draw a structure for each of the following:
c. o-nitroaniline
문제 10d
Draw a structure for each of the following:
d. m-chlorobenzonitrile
문제 11c
Draw a structure for each of the following:
c. 4-bromo-3-chloroaniline
문제 12a
Correct the following incorrect names:
a. 2,4,6-tribromobenzene
문제 12b
Correct the following incorrect names:
b. 3-hydroxynitrobenzene
문제 12c,d
Correct the following incorrect names:
c. para-methylbromobenzene
d. 1,6-dichlorobenzene
문제 12e,f
Correct the following incorrect names:
e. meta-bromotoluene
f. 6-ethyl-4-iodoaniline
문제 14
Explain why fluorobenzene is more reactive than chlorobenzene toward electrophilic aromatic substitution but chloromethylbenzene is more reactive than fluoromethylbenzene.
문제 15a
List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:
a. benzene, phenol, toluene, nitrobenzene, bromobenzene
문제 15b
List the compounds in each set from most reactive to least reactive toward electrophilic aromatic substitution:
b. dichloromethylbenzene, difluoromethylbenzene, toluene, chloromethylbenzene
문제 16a
Draw the resonance contributors for:
a. benzaldehyde
문제 17e,f
What product(s) result from nitration of each of the following?
e. benzenesulfonic acid
f. cyclohexylbenzene
- For each horizontal row of substituted benzenes, indicate b. the one that is the least reactive in an electrophilic aromatic substitution reaction.
문제 18
문제 18a,b,c
Are the following substituents ortho–para directors or meta directors?
a. CH=CHC≡N
b. NO2
c. CH2OH
문제 18d,e,f
Are the following substituents ortho–para directors or meta directors?
d. COOH
e. CF3
f. N=O
문제 20a
What products are obtained from the reaction of the following compounds with one equivalent of Br2, using FeBr3 as a catalyst?
a.
문제 20b
What products are obtained from the reaction of the following compounds with one equivalent of Br2, using FeBr3 as a catalyst?
b.
문제 20c,d
What products are obtained from the reaction of the following compounds with one equivalent of Br2, using FeBr3 as a catalyst?
c.
d.
문제 21a,b
Give the products, if any, of each of the following reactions:
a. benzonitrile + methyl chloride + AlCl3
b. phenol + Br2
문제 21c,d
Give the products, if any, of each of the following reactions:
c. benzoic acid + CH3CH2Cl + AlCl3
d. benzene + 2 CH3Cl + AlCl3
문제 22
a. Does a coupling reaction have to be used to synthesize p-dipropylbenzene?
b. Can a coupling reaction be used to synthesize p-dipropylbenzene?
문제 23a
Show how the following compounds can be synthesized from benzene:
a.
문제 23b
Show how the following compounds can be synthesized from benzene:
b.
문제 24a
Show how each of the following compounds can be synthesized from benzene:
a. o-bromopropylbenzene
문제 24d
Show how each of the following compounds can be synthesized from benzene:
d. p-chloroaniline
문제 24f
Show how each of the following compounds can be synthesized from benzene:
f. m-xylene
문제 24g
Show how each of the following compounds can be synthesized from benzene:
g. 2-phenylpropene
문제 24h
Show how each of the following compounds can be synthesized from benzene:
h. m-bromopropylbenzene
