10/8/14

Gugus  Fungsi  

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•  Alkenes  
•  Ethene  (ethylene)  is  a  major  industrial  feedstock  
•  Used  in  the  produc=on  of  ethanol,  ethylene  oxide  and  the  polymer  
polyethylene  
 
 
 
 
 
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•  Propene  (propylene)  is  also  very  important  in  industry  
•  Molecular  formula  C3H6  
•  Used  to  make  the  polymer  polypropylene  and  is  the  star=ng  material  for  
acetone  
•  Many  alkenes  occur  naturally  

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•  Alkynes  
•  Ethyne  (acetylene)  is  used  in  welding  torches  because  it  burns  at  high  
temperature  
 
•  Many  alkynes  are  of  biological  interest  
•  Capillin  is  an  an=fungal  agent  found  naturally  
•  Dactylyne  is  a  marine  natural  product  
•  Ethinyl  estradiol  is  a  synthe=c  estrogen  used  in  oral  contracep=ves  

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•  Benzene:  A  Representa=ve  Hydrocarbon  

•  Benzene  is  the  prototypical  aroma=c  compound  
•  The  Kekulé  structure  (named  aRer  August  Kekulé  who  formulated  it)    is  
a  six-­‐membered  ring  with  alterna=ng  double  and  single  bonds  
 

 
 
 
 
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•  Benzene  does  not  actually  have  discreet  single  and  double  
carbon-­‐carbon  bonds  
•  All  carbon-­‐carbon  bonds  are  exactly  equal  in  length  (1.38  Å)    
•  This  is  between  the  length  of  a  carbon-­‐carbon  single  bond  and  a  
carbon-­‐carbon  double  bond    
•  Resonance  theory  explains  this  by  sugges=ng  there  are  two  
resonance  hybrids  that  contribute  equally  to  the  real  structure  
•  The  real  structure  is  oRen  depicted  as  a  hexagon  with  a  circle  in  the  
middle  

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Some  Well-­‐known  Aroma/c  Compounds  

CO 2H O
OCCH3

acetyl salicylic acid

ibuprofin
HO 2C
HO 2C CH3

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N O
CH2CNH S
N
CH3
NH penicillin G CO H
N 2
lysergic acid

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OH
O
morphine
OH

 -­‐  Alkyl  Halides  

In  alkyl  halides,  a  halogen  (F,  Cl,  Br,  I)  
replaces  the  hydrogen  of  an  alkane  
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•  Alkohol  
•  In  alcohols  the  hydrogen  of  the  alkane  is  replaced  by  the  hydroxyl  (-­‐
OH)  group  
•  An  alcohol  can  be  viewed  as  either  a  hydroxyl  deriva=ve  of  an  alkane  or  an  
alkyl  deriva=ve  of  water  
 

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•  Alcohols  are  also  classified  according  to  the  carbon  the  hydroxyl  is  
directly  a\ached  to  

Beberapa  contoh  Alkohol  

OH OH
CH3CH2OH HO CHCH2NH2 CHCHNHCH3
CH3
ethanol HO adrenaline pseudephidrine
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OH
HOCH2CHCH2OH
glycerol cholesterol

HO 8

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Alcohols  are  Found  in  Many  Natural  Products  

HO

O N CH3

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H
HO
Morphine
most abundant of opium's alkaloids
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CH3 CH3
N N Designer  Drugs  

OH OH
O O
OH OCH3
morphine codeine
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CH3 CH3
N N

O OAc
O O
OCH3 OAc
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oxycodone heroin
oxycontin (slow release)
percocet (w/ acetominophen)

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•  Ethers  
•  Ethers  have  the  general  formula  R-­‐O-­‐R  or  R-­‐O-­‐R’  where  R’  is  different  
from  R  
•  These  can  be  considered  organic  deriva=ves  of  water  in  which  both  
hydrogens  are  replaced  by  organic  groups    
•  The  bond  angle  at  oxygen  is  close  to  the  tetrahedral  angle  
 
 

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•  Amines  
•  Amines  are  organic  deriva=ves  of  ammonia    
•  They  are  classified  according  to  how  many  alkyl  groups  
replace  the  hydrogens  of  ammonia  
•  This  is  a  different  classifica=on  scheme  than  that  used  in  
alcohols  
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– Aldehydes  and  Ketones  

•  Both  contain  the  carbonyl  group  
 
 
 
•  Aldehydes  have  one  carbon  a\ached  to  the  carbonyl  group  
 
 
 

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•  Ketones  have  two  organic  groups  a\ached  to  the  carbonyl  
group  
 

 
•  The  carbonyl  carbon  is  sp2  hybridized    
–  It  is  trigonal  planar  and  has  bond  angle  about  120o  

Adrogenic/Anabolic  Steroids  

CH3 OH CH3 O

CH3 H CH3 H
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H H H H
O O
Testosterone Androstenedione

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•  Carboxylic  Acids,  Esters  and  Amides  

•  All  these  groups  contain  a  carbonyl  group  bonded  to  an  oxygen  or  
nitrogen  
•  Carboxylic  Acids  
•  Contain  the  carboxyl  (carbonyl  +  hydroxyl)  group  
 

 
•  Esters  

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•  A  carbonyl  group  is  bonded  to  an  alkoxyl  (OR’)  group  
 

Analgesics  

CO2H O
OCCH3
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(S)(+)-
acetyl salicylic acid ibuprofin
HO2C

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Fats  and  FaBy  Acids  

CO2H
palmitic acid (a fatty acid)
O

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CH2 OCR
O
CH OCR
O
CH2 OCR R = n-C15H31
a triglyceride
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From  Ergot  Fungus  

HO2C CH3
N
H
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(+) lysergic acid

NH 18

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Func/onal  Groups  
link  to  Carey”s  site  

(CH3)2N
O O
OH
H2NCHCNHCHCOCH3
C CH

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HOCCH 2 CH2

O
O
Mifepristone (RU-486) Aspartame

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•  Amide  
•  A  carbonyl  group  is  bonded  to  a  nitrogen  derived  from  ammonia  or  an  
amine  

•  Nitriles    
•  An  alkyl  group  is  a\ached  to  a  carbon  triply  bonded  to  a  nitrogen  
•  This  func=onal  group  is  called  a  cyano  group  

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 Summary  of  Important  Families  of  Organic  Compounds  

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Summary  (cont.)  
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From  the  Bark  of  the    

Pacific  Yew  Tree   O
O O OH

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O NH O
O
O
OH O O
OH
O
O 23

Taxus brevifolia

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