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Chemistry 1102
Charlie Bond
MCS Rm 4.16/4.27
[email protected]
What is Organic Chemistry?
Organic Reactions I II
Alanes !Ch 21"
Con#ormational Analysis !Ch 21"
$tereochemistry I II III !Ch 22"
Alkyl Halides I II !Ch 2%"
Alcohols and &ther I II !Ch 2%"
mailto:[email protected]:[email protected]
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Problems from Brown&LeMay
Chaper 24
!ll "#es$ons %oer le%#res '(12
!l)yl hal$*es "#es$ons are owar*s heen*+ al%ohols owar*s he
sar
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Sr#%#re
-aloal)ane al)yl hal$*e-aloal)ane al)yl hal$*e00 a %ompo#n*
%ona$n$n a haloen aom %oalenly
bon*e* o an s',hybr$*$e* %arbon
3 $en he symbol R
A haloalkane(an alkyl halide)
R X
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5omen%la#re ( P!C3
lo%ae he paren al)ane3 n#mber he paren %ha$n o $e he
s#bs$#en
en%o#nere* f$rs he lower n#mber
3 show haloen s#bs$#ens by he pref$8es fl#oro(+
%hloro(+ bromo(+ an* $o*o( an* l$s hem $nalphabe$%al or*er w$h
oher s#bs$#ens
3 lo%ae ea%h haloen on he paren %ha$n
3-Bromo-2-methyl-pentane
12345
Br
4-Bromocyclohexene
1
23
4
5
6Br
OH
Cl
trans-2-Chloro-cyclohexanol
4
56
1
23
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5omen%la#re
seeral polyhaloal)anes are %ommon
solens an* are enerally referre* o by
he$r %ommon or r$$al names
Dichloromethane(Methylene chloride)
Trichloromethane(Chloroform)
Trichloroethylene(Trichlor)
, , -Trichloroethane111(Methyl chloroform)
CHCl3CH2 Cl2
CCl2=CHClCH3 CCl3
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:reons & ;he$r !lerna$es ;he :reons are %hlorofl#oro%arbons
C:Cs
3 amon he mos w$*ely #se* are/were
3 ! a 1',< !CS mee$n+ ;homas M$*eley anno#n%e* hesynhes$s of
*$%hlorofl#oromehane. -e $nhale* he apors an*blew a %an*le o#+ h#s
*emonsra$n ha $ was ne$her o8$%nor flammable=
3 m#%h lower oone(*eple$n alerna$es are hehy*rofl#oro%arbons
-:Cs an* he hy*ro%hlorofl#oro%arbons-C:Cs+ $n%l#*$n
CClF CClF
Trichlorofluoromethane(Freon-11)
Dichlorodifluoromethane(Freon-12)
CH2FCF3 CH3CCl2F
HFC-134a HCFC-141b
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S#bs$#$on & >l$m$na$on !l)yl hal$*es are #se* o *emonsrae
2 ypes of rea%$on
3 n#%leoph$l$% s#bs$#$on
(el$m$na$on
Br
H
EtO-Na
+
OEt
EtOH
Na+Br
-
Na+Br
-
ethanol
ethanol
+
+
+
as a nucleophile,
ethoxide ion attacksthis carbon
a nucleophileand a base
as a base, ethoxide ionattacks this hydrogen
+
nucleophilicsubstitution
-elimination
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5#%leoph$l$% S#bs$#$on
Some n#%leoph$l$% s#bs$#$on rea%$ons
CH3-I
HO-
Nu-
RO-
HS-
RS-
I-
NH3
HOH
CH3-SH
CH3-SR
CH3-OH
CH3-OR
H
CH3-O-H
CH3-NH3+
CH3X CH3Nu X-
+
An alcohol (after proton transfer)
An alkylammonium ion
An alkyl iodide
A sulfide (a thioether)
A thiol (a mercaptan)
An ether
An alcohol
Reaction: + +
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