CP203 LecLure 24

CcLober 29, 2014

1wenLy quesuons


2
Addluon Lo alkenes
3
Markovnlkov's rule rule sLaLes LhaL ln Lhe addluon of Px Lo an unsymmeLrlcal alkene,
Lhe hydrogen becomes auached Lo Lhe carbon wlLh fewer alkyl subsuLuenLs, and Lhe
hallde becomes auached Lo Lhe carbon wlLh more alkyl subsuLuenLs.
vladlmlr vasllyevlch Markovnlkov
8adlcal addluon of P8r Lo alkenes
4
Br
HBr
H
H
Br Markovnlkov addluon
non-Markovnlkov addluon
Addluon of PCl and Pl glves only Markovnlkov producLs. Addluon of P8r glves one or
Lhe oLher dependlng on Lhe reacuon condluons.
8adlcal addluon of P8r Lo alkenes
3
Careful observauon showed LhaL Lhe non-Markovnlkov addluon of P8r happened ln
Lhe presence of peroxldes. ChemlsLs Lherefore proposed a radlcal chaln mechanlsm.
8adlcal addluon of P8r Lo alkenes
6
1ermlnauon sLeps. Cne generaLes an unwanLed dlbromo lmpurlLy.
8adlcal addluon of P8r Lo alkenes
7
8oLh mechanlsms are regloselecuve. 1he radlcal mechanlsm ma[or producL comes
from Lhe addluon of a bromlne radlcal Lo Lhe double bond Lo glve Lhe more sLable 3
o

carbon radlcal. 1he polar mechanlsm ma[or producL comes from Lhe addluon of P
+
Lo
Lhe double bond Lo glve Lhe more sLable 3
o
carbon cauon.
WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon lf a radlcal
lnhlblLor ls added?





WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon lf a radlcal
lnhlblLor ls added?



WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon lf a radlcal
lnhlblLor ls added?




WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon lf a radlcal
lnhlblLor ls added?


WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon?

WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon?

Whlch of Lhe followlng accounLs for Lhe anu-Markovnlkov reglochemlsLry of Lhe
reacuon of an alkene wlLh P8r ln Lhe presence of peroxldes?

a. 1he alkene reacLs wlLh P8r Lo glve a carbocauon.
b. 1he alkene reacLs wlLh a bromlne aLom Lo glve a radlcal.

c. 1he alkene reacLs wlLh a hydrogen aLom Lo glve a radlcal.

d. 1he alkene reacLs wlLh peroxlde Lo glve an allyllc radlcal.

Whlch of Lhe followlng accounLs for Lhe anu-Markovnlkov reglochemlsLry of Lhe
reacuon of an alkene wlLh P8r ln Lhe presence of peroxldes?

a. 1he alkene reacLs wlLh P8r Lo glve a carbocauon.
b. 1he alkene reacLs wlLh a bromlne aLom Lo glve a radlcal.

c. 1he alkene reacLs wlLh a hydrogen aLom Lo glve a radlcal.

d. 1he alkene reacLs wlLh peroxlde Lo glve an allyllc radlcal.

WhaL are Lhe ma[or producLs formed upon LreaLmenL of (!)-3-meLhyl-2-hexene
wlLh P8r ln Lhe absence of peroxldes?

!" (")-2-bromo-3-meLhylhexane
#" (#)-3-bromo-2-meLhylhexane
$" 3-bromo-3-meLhylhexane

a. only !
b. only #
c. a mlxLure of ! and #
d. only $

WhaL are Lhe ma[or producLs formed upon LreaLmenL of (!)-3-meLhyl-2-hexene
wlLh P8r ln Lhe absence of peroxldes?

!" (")-2-bromo-3-meLhylhexane
#" (#)-3-bromo-2-meLhylhexane
$" 3-bromo-3-meLhylhexane

a. only !
b. only #
c. a mlxLure of ! and #
d. only $

H H
Br
H
+ Br
-
WhaL ls Lhe luAC name of Lhe followlng compound?









a. (#)-1-chloro-3-meLhyl-2-cyclohexene
b. (")-1-chloro-3-meLhyl-2-cyclohexene
c. (#)-3-chloro-1-meLhylcyclohexene
d. (")$3-chloro-1-meLhylcyclohexene




WhaL ls Lhe luAC name of Lhe followlng compound?









a. (#)-1-chloro-3-meLhyl-2-cyclohexene
b. (")-1-chloro-3-meLhyl-2-cyclohexene
c. (#)-3-chloro-1-meLhylcyclohexene
d. (")$3-chloro-1-meLhylcyclohexene




Whlch of Lhe followlng alkenes undergoes allyllc bromlnauon Lo form a slngle
monobromlnaLed producL?







a. !
b. #
c. $
d. %



Whlch of Lhe followlng alkenes undergoes allyllc bromlnauon Lo form a slngle
monobromlnaLed producL?







a. !
b. #
c. $
d. %



Whlch of Lhe followlng sLaLemenLs ls %&' Lrue regardlng Lhe halogenauon of
alkanes upon LreaLmenL wlLh halogen and llghL?

a. 8romlnauon ls more selecuve for 3 posluons Lhan chlorlnauon.
b. 1he reacuon proceeds vla a radlcal lnLermedlaLe.
c. 1he reacuon proceeds vla a chaln reacuon.
d. 1hls ls a useful process for Lhe formauon of uorldes, chlorldes, bromldes and
lodldes.


Whlch of Lhe followlng sLaLemenLs ls %&' Lrue regardlng Lhe halogenauon of
alkanes upon LreaLmenL wlLh halogen and llghL?

a. 8romlnauon ls more selecuve for 3 posluons Lhan chlorlnauon.
b. 1he reacuon proceeds vla a radlcal lnLermedlaLe.
c. 1he reacuon proceeds vla a chaln reacuon.
d. 1hls ls a useful process for Lhe formauon of uorldes, chlorldes, bromldes and
lodldes.


Whlch of Lhe followlng compounds ls mosL suscepuble Lo auLoxldauon?

a. propene
b. 1,3-buLadlene
c. 1,4-penLadlene
d. 1,3-hexadlene
Whlch of Lhe followlng compounds ls mosL suscepuble Lo auLoxldauon?

a. propene
b. 1,3-buLadlene
c. 1,4-penLadlene
d. 1,3-hexadlene
WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon?









a. !
b. #
c. $
d. %


WhaL ls Lhe ma[or organlc producL obLalned from Lhe followlng reacuon?









a. !
b. #
c. $
d. %


Pow many seLs of equlvalenL proLons are Lhere ln 2-meLhylhexane?

a. 2
b. 3
c. 6
d.7

Pow many seLs of equlvalenL proLons are Lhere ln 2-meLhylhexane?

a. 2
b. 3
c. 6
d.7

WhaL ls Lhe spllmng of Lhe slgnal ln Lhe
1
P nM8 specLrum for Lhe meLhyl proLons
of propane?


a. slngleL
b. doubleL
c. LrlpleL
d. quarLeL

WhaL ls Lhe spllmng of Lhe slgnal ln Lhe
1
P nM8 specLrum for Lhe meLhyl proLons
of propane?


a. slngleL
b. doubleL
c. LrlpleL
d. quarLeL

Whlch C
4
P
9
8r compound glves a doubleL aL approxlmaLely 3.3 ppm ln Lhe
1
P nM8
specLrum?







a. !
b. #
c. $
d. %




Whlch C
4
P
9
8r compound glves a doubleL aL approxlmaLely 3.3 ppm ln Lhe
1
P nM8
specLrum?







a. !
b. #
c. $
d. %




Pow many slgnals appear ln Lhe proLon-decoupled
13
C nM8 specLrum of 1,4-
dlbromobenzene?

a. 1
b. 2
c. 3
d. 4



Pow many slgnals appear ln Lhe proLon-decoupled
13
C nM8 specLrum of 1,4-
dlbromobenzene?

a. 1
b. 2
c. 3
d. 4



Pow many slgnals appear ln Lhe proLon-decoupled
13
C nM8 specLrum of 1,2-
dlbromobenzene?

a. 1
b. 2
c. 3
d. 4



Pow many slgnals appear ln Lhe proLon-decoupled
13
C nM8 specLrum of 1,2-
dlbromobenzene?

a. 1
b. 2
c. 3
d. 4



Whlch of Lhe followlng compounds would glve a
1
P nM8 specLrum conslsung of
Lwo slngleLs and a
13
C nM8 conslsung of conslsung of Lhree slgnals?









a. only (
b. only (((
c. only ( and (((
d. ((( and ()


Whlch of Lhe followlng compounds would glve a
1
P nM8 specLrum conslsung of
Lwo slngleLs and a
13
C nM8 conslsung of conslsung of Lhree slgnals?









a. only (
b. only (((
c. only ( and (((
d. ((( and ()


Aromauc
1own
CounLy
vlnyl
AceLonlsh
Alkyl
ClLy
Pere be monsLers and aldehydes
Aromauc
1own
CounLy
vlnyl
AceLonlsh
Alkyl
ClLy
Pere be monsLers and aldehydes
H
N
O
O
O
O
N
H
N
+
O

O
Whlch of Lhe carbon aLoms ln Lhe followlng molecule appears aL Lhe hlghesL ppm
ln Lhe
13
C nM8 specLrum?






a. (
b. ((
c. (((
d. ()



Whlch of Lhe carbon aLoms ln Lhe followlng molecule appears aL Lhe hlghesL ppm
ln Lhe
13
C nM8 specLrum?






a. (
b. ((
c. (((
d. ()



Whlch C
9
P
10
C compound glves Lhe followlng
1
P nM8 specLrum?

a. 1
b. 2
c. 3
d. 4




Whlch C
9
P
10
C compound glves Lhe followlng
1
P nM8 specLrum?

a. 1
b. 2
c. 3
d. 4




Whlch C
8
P
10
compound glves Lhe followlng
1
P nM8 specLrum?

a. 1
b. 2
c. 3
d. 4




Whlch C
8
P
10
compound glves Lhe followlng
1
P nM8 specLrum?

a. 1
b. 2
c. 3
d. 4




ldenufy Lhe compound (C
8
P
10
) LhaL glves Lhe followlng
1
P nM8 specLrum.

ldenufy Lhe compound (C
8
P
10
) LhaL glves Lhe followlng
1
P nM8 specLrum.

1,2-ulmeLhylbenzene,
&-xylene
ldenufy Lhe compound (C
4
P
8
C ) LhaL glves Lhe followlng
1
P nM8 specLrum.

ldenufy Lhe compound (C
4
P
8
C ) LhaL glves Lhe followlng
1
P nM8 specLrum.

8uLanal