CHEM 2322 Navarro College Organic Chemical Reactions Mechanism Isoprene undergoes electrophilic addition of HBr to give several products – identify these p

CHEM 2322 Navarro College Organic Chemical Reactions Mechanism Isoprene undergoes electrophilic addition of HBr to give several products – identify these products and draw a mechanism which accounts for ALL of these adducts. If this reaction were conducted under kinetic conditions, which adduct would be favored?Anisole undergoes electrophilic aromatic substitution with chlorine and ferric chloride to afford a mixture rich in o- and p-chloroanisoles. Write a mechanism that accounts for the formation of these products – include electrophile formation as well as any steps involving the aromatic ring. Indicate, which is the major product and explain why.Using the spectroscopic data provided below, determine the structure of the unknown compound. Fully justify your answer with supporting information from each piece of spectroscopic data – just writing a structure is insufficient. 1. Isoprene undergoes electrophilic addition of HBr to give several products – identify these products and draw a
mechanism which accounts for ALL of these adducts. If this reaction were conducted under kinetic conditions,
which adduct would be favored?
HBr
2. Anisole undergoes electrophilic aromatic substitution with chlorine and ferric chloride to afford a mixture rich in
0- and p-chloroanisoles. Write a mechanism that accounts for the formation of these products – include
electrophile formation as well as any steps involving the aromatic ring. Indicate, which is the major product and
explain why.
CI
CI
Cl2, FeCl3
CI
OMe
?Me
OMe
OMe
3. Using the spectroscopic data provided below, determine the structure of the unknown compound. Fully justify
your answer with supporting information from each piece of spectroscopic data – just writing a structure is
insufficient.
?
3326
1085
IR Spectrum
(CHCl3 solution)
4000
3000
1200
800
2000 1600
V (cm)
10n
107
Macs Snectrum
Grade
3. Using the spectroscopic data provided below, determine the structure of the unknown compound. Fully justity
your answer with supporting information from each piece of spectroscopic data – just writing a structure is
insufficient.
??
para
3326
1085
IR Spectrum
(CHCl3 solution)
4000
3000
1200
800
2000 1600
V (cm)
107
Mass Spectrum
100
80
60
% of base peak
40
M+ = 138
20
121
40
80
200
240
280
120 160
m/e
13C NMR Spectrum
(100.0 MHz, CDCi, solution)
DEPT CH2 CH3 CH
solvent
proton decoupled
200
160
120
80
40
08 (ppm)
TH NMR Spectrum
(400 MHz, CDCI, solution)
SSS
7.5
7.0 ppm
Exchanges
with D20
TMS

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