19 ch203 fall 2014 lecture 19 october 17.pdf

8/10/2019 19 CH203 Fall 2014 Lecture 19 October 17.pdf

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!"# %&'() *+,-. /0'1)+- &-2 30) 4"0(-2) !"# 5(063 &-2 !"# !,-7&- '(6(8("9 (8(-0-. 0- !"# /0'1)+-:) ;20-


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H( =08(2#


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IHJKL M(76,"( ENA76+


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H&=+&=P&-()

C

Haloalkanes, or alkyl halides, are alkanes containing a halogen atom

bonded to an sp3hybridized carbon atom.

Alkyl halides are classified as primary (1), secondary (2), or tertiary

(3), depending on the number of carbons bonded to the carbon withthe halogen atom.

The halogen atom is often represented generically as X.


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6/32

A63(" +".&-07 3&=02()

T

O- &==9= U+" &==9=07V 3&=02( 7+-6&0-) & 3&=+.(-


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A".&-07 3&=02() Y -+'(-7=&6,"(

G


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A".&-07 3&=02() Y -+'(-7=&6,"(

F

Br

2-Bromo-4-methyl-pentane

12

34

5

4-Bromo-cyclohexene

1

23 4

5

6

trans-2-Chloro-cyclohexanol

Br l

O

Z[\OI -&'()#

/+'( )0'1=( +".&-07 3&=02() 3&8( 7+''+- -&'()#

r

l

l

2-Bromobutane

(sec

-Butyl bromide)

Chloroethene

(Vinyl chloride)

3-Chloropropene

(Allyl chloride)


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A".&-07 3&=02() Y -+'(-7=&6,"(

N

/+'( 1+=93&=+&=P&-() &"( 0-2,)6"0&= +" =&


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A".&-07 3&=02()

EK

\+=96(6"&],+"+(639=(-( U\^_;V 0) & )9-63(?7 ],+"+1+=9'(" +4 6(6"&],+"+(639=(-(#

!,\+-6D 63( 0-8(-6+"D )(==) \^_; ,-2(" 63( 6"&2(-&'( ^(]+-#


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A".&-07 3&=02()

EE

\("],+"++76&-+07 &702 U\_AOV 0) & )9-63(?7 1("],+"0-&6(2 7&"


12/32

A".&-07 3&=02()

EJ

!0(639= (63(" U&&) c")6 2('+-)6"&6(2 &) &- &-()63(?7 0- 63( ;63(" !+'( &6

d&))&73,)(e) f(-("&= H+)106&=# ;63(" >&) -07P-&'(2 63( g*&-P(( !+2.(h &)

',73 '+"( (@(7?8( 63&- '()'("0)'D +" 391-+)0)D &6 ("( )9-63()0R(2


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A".&-07 3&=02()

EL

EN_ 3&) & )10- +4 i &-2 7+'1"0)() EKKj +4 -&6,"&==9 +77,""0-. ],+"0-(# A63("

3&=+.(- 0)+6+1() 7&1&


14/32

\"+1("?() +4 3&=+&=P&-() m 201+=( '+'(-6

EC

H

C X

H

H

!+ !-

H

C X

H

H

n3(- 6>+ 1&"?&= +11+)06( 73&".() &"( )(1&"&6(2D & 201+=( '+'(-6 o &"0)()#

^3( '&.-06,2( +4 o 0-7"(&)() &) 63( 1&"?&= 73&".( 0-7"(&)() &-2 &) 63( 20)6&-7(

((- 63(' 0-7"(&)()#


15/32

\"+1("?() +4 3&=+&=P&-() m 201+=( '+'(-6

EQ

H

C X

H

H

!+ !-

H

C X

H

H

Z- & 7&"


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17/32


18/32

\"+1("?() +4 3&=+&=P&-()

EF

U&V 0) & 5(()+' 4+"7( ((- 6>+ '+=(7,=() >063 1("'&-(-6 201+=()#

U


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\"+1("?() +4 3&=+&=P&-()

EN

^>+ (=(76"+- 7=+,2)D (063(" &- &6+' +" ."+,1 +4 &6+')D >0== &e"&76 +-( &-+63(" &6 &

20)6&-7( 2,( 6+ 63( 8&- 2(" n&&=) 4+"7()# O6 )+'( 1+0-6D 63( (=(76"+- 7=+,2) >0==

+8("=&1 &-2


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\"+1("?() +4 3&=+&=P&-()

JK

I+8&=(-6 7=+)( 6>+ -+-Y


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Boiling Points

The size of Br and CH3about the same but bromo compounds boil

higher due to greater polarizability; more dispersion forces.


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Boiling Points

Branching in an alkane decreases the boiling point. Likewise for

haloalkanes.


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Boiling Points

Fluoroalkanes and alkanes of same MW have about the same BP. In

both cases the electrons are tightly held, not very polarizable.


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\"+1("?() +4 3&=+&=P&-() Y 1+=&"0R&3073 63( (=(76"+- 2(-)069 &


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Scheme 1.Development of Ezetimibe (SCH58235) by optimization of the lead

SCH48461.[12,13] As part of the optimization, two metabolically labile sites are blocked by flu-orine substituents.

Z-7+"1+"&?+- +4 & ],+"0-( &6+' 7&-


26/32

\"+1("?() +4 3&=+&=P&-() m ],+"0-&6(2 2",.)

d(6&


27/32

\"+1("?() +4 3&=+&=P&-() m 2(-)0?()

JG


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29/32


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\"+1("?() +4 3&=+&=P&-()

LK


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\"+1("?() +4 3&=+&=P&-() m


32/32

\"(1&"&?+- +4 3&=+&=P&-() m 3&=+.(-&?+- +4 &=P&-()

LJ

C H

H3C

H3C

H3C

C H

H3C

H3C

H3C

C H

H3

C

H3C

H3C

C H

H3C

H3C

H3C

F2

Cl2

Br2

I2

+

+

+

+

C Cl

H3C

H3C

H3C

C Br

H3C

H3C

H3C

C H

H3C

H3C

H3C I2+

HCl+

HBr+

19 ch203 fall 2014 lecture 19 october 17.pdf

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