Organic Chemistry
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Organic Chemistry
BELL RINGER
What makes a compound
organic?
Origin of organic compoundsOrigin of organic compounds• Naturally occurring organic compounds are
found in plants, animals, and fossil fuels• All of these have a plant origin• All of these rely on the “fixing” of C from CO2
• Synthetic organic compounds are derived from fossil fuels or plant material
IntroductionIntroduction• Most current research focuses on Organic • Originally from “organic” meaning life• Not just chemistry of life, chemistry of carbon• Exceptions:
– oxides of carbon (CO2, CO)
– carbonates,bicarbonates(NaHCO3,CaCO3)– cyanides (NaCN, etc)
C C CCC
One C with no H, or with metal
• Carbon can form four bonds…
Properties of Organic CompoundsProperties of Organic Compounds
1. Covalently bonded2. Low Melting Points3. Non-electrolytes4. Nonpolar5. React slower than inorganic compounds6. Require high activation energies7. Insoluble in water ~ generally
Carbon forms four bondsCarbon forms four bonds• Carbon can form four bonds, and forms
strong covalent bonds with other elements• This can be represented in many ways …
CH C
C CH
CH CH
Cl
Cl
CH3 CH3
CH3
CH3
CH3
CH3
CH3
CH2CH2
CH2CH2
CH2CH2
CH2CH2
CH3
C
CO
C
C
Cl
HH
H
Functional groupsFunctional groups• Functional groups are parts of molecules that
result in characteristic features• About 100 functional groups exist, we will
focus on about 10• Useful to group the infinite number of possible
organic compounds• Ex - the simplest group is hydrocarbons
• Made up of only C and H• Not really a functional “group”• Further divided into:
»Aliphatics - Alkanes, Alkenes, Alkynes»Aromatics
HydrocarbonsHydrocarbonsC C C C
C C
C
C
C
C
C
C
H
H
H
H
H
H
C C C C C
H
H
H
H
H H
H
H
H
H
H
H
Alkanes Alkenes
Alkynes Aromatics
C C C C C
H
H
H
H
H
H
H
H
H
H
C C C C CH
H
H
H
H
H
H
H
CnH2n+2 CnH2n
CnH2n-2
Naming Hydrocarbons (nomenclature)
Drawing structures: it’s all good
CH3
CH
CH
CH3
CH3
CHCH
CH3
2-butene
This is called the “condensed structure”
C C C C
H
H
H
H H H
H
H
CH3 CH CH CH3
On a test, choose a method that shows all H’s
CH3CH=CHCH3
Using brackets can also shorten some formulas: CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3
Draw/Name the following
Octane
1-hexyne
Propene
C C C C C C C C
H
H
H
H H H
H H H H H
H
H
HHH
HH
C C C
H
H H
H
HH
C C C C CH
H H H
H
H
HH
HH
C C C C C CH
H H H
H H
H
H
HH
2-pentene
BELL RINGER
What is the structural formula for 2-hexene
CH3CHCHCH2CH2CH3
Hydroxyl, carbonyl, carboxylHydroxyl, carbonyl, carboxyl
• There are other names that describe patterns of atoms that are parts of functional groups.
• “Hydroxyl” refers to –OH
• “Carbonyl” refers to C=O
• “Carboxyl” refers to COOH
Naming: common vs. IUPAC• Common names used in the 1800’s are still
used for some compounds today:
H C C HAcetylene
O
CCH3CH3
AcetoneFormic acid
C
O
OHH
• The International Union of Pure and Applied Chemistry (IUPAC) was established in 1900s
Numbering carbonsQ- draw penteneA- Where’s the bond?
We number C atoms
• Thus, naming compounds with multiple bonds is more complex than previously indicated
• Only if 2+ possibilities exist, are #s needed• Always give double bond the lowest number• Try to name these:
C C C CCH3
H
H
H
H H H
HCH31
C2
C3
C4
C5
H
H
H
H H H
HCH35
C4
C3
C2
C1
H
H
H
H H H
H
Ethene
3-nonyne
2-butene
1-pentene
CH3CH
CH
CH3
C2H4
CH3CH2CCCH2CH2CH2CH2CH3
CH3 CH3
CH3
CH3Branched Hydrocarbons
• Names are made up of: side chains, root
• Root is the longest possible HC chain• Must contain multiple bonds if present• Add -yl to get name of side chain• Common side chains include:
CH3- methyl CH3CH2- ethyl
CH3CH2CH2- propyl (CH3)2CH- isopropyl
• 2,3-dimethylpentane
CH3 CH3
CH3
CH3
CH3CH
CH3
*
• Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)
-ane
Naming side chains
CH3 CH2 CH
CH3
CH2 C
CH2
CH3
CH3
CH3
Rule 1: choose the correct ending
ane
Rule 2: longest carbon chain
Naming side chains
CH3 CH2 CH
CH3
CH2 C
CH2
CH3
CH3
CH3
aneHeptane
Rule 3: attach prefix (according to # of C)
Naming side chains
CH3 CH2 CH
CH3
CH2 C
CH2
CH3
CH3
CH3
Rule 4: Assign numbers to each carbon
CH3 CH2 C6
CH3
7CH2
5C
4
CH2
CH3
CH3
CH3
CH3 CH2 CH CH2 C
CH2
CH3
CH3
CH3
heptane
Naming side chains
2 1
3
CH3 CH2 C
CH
CH2 C
CH2
CH3
CH3
CH3
Rule 5: Determine name for side chains
CH3 CH2 CH
3
CH2 C
CH2
CH3
CH3
CH3
Naming side chains
methyl
methyl
methyl
heptane
67 5 4 3
2 1
CH3 CH2 CH
CH3
CH2 C
CH2
CH3
CH3
CH3
3-methyl-3-methyl-5-methyl-heptane
Naming side chains
methyl
methyl
methyl
Rule 6: attach name of branches
67 5 4 3
2 1
Rule 8,9: group similar branches
CH3 CH2 CH
CH3
CH2 C
CH2
CH3
CH3
CH3
3-methyl-3-methyl-5-methyl-heptane
Naming side chains
methyl
methyl
methyl
67 5 4 3
2 1
Rule 8,9: group similar branches
CH3 CH2 CH
CH3
CH2 C
CH2
CH3
CH3
CH3
3,3,5-trimethyl-heptane
Naming side chains
methyl
methyl
methyl
67 5 4 3
2 1
BELL RINGERName the
hydrocarbon
C – C – C – C = C – C
C C
H
C C
C HH
H
H
H
HH
H
HH
H
HHHH
HH H
H HH 4-ethyl-3-methyl-4-octene
Naming side chains
CH3 CH2
CH CH3
CH2CH2
CH3
CH3 CH
CH
CH3
CH
CH3
CH2 CH2 CH3
CH2 CH3
CH3CH2CH CH CH CH2CH CH3
CH3
CH2CH3
CH3 CH3
3-methylhexane4-ethyl-2,3-dimethylheptane
5-ethyl-2,4,6-trimethyloctane
Functional GroupsAlcohols
-OHElement Grouping:
Example:
Naming: -name ends in –ol
CHCH2CH3 CH3
OH
2-butanol
Functional GroupsAlcohols
Ethylene glycol 1,2 Ethanediol
CHO C
H
OH
H
H H
Odorless, colorless, sweet and syrupy, toxic liquid
Functional GroupsAldehydes
Element Grouping:
Example:
Naming: -name ends in –al
ethanal
C
O
H
CH3 C
O
H
Functional GroupsKetones
Element Grouping:
Example:
Naming: -name ends in –one
propanone
C
O
CH3 C CH3
O
Functional GroupsOrganic Acids
Element Grouping:
Example:
Naming: -name ends in –oic acid
butanoic acid
OHC
O
CH2CH2CH3 C
O
OH
BELL RINGERName the following organic compound:
3-hexanone
C – C – C – C – C – C H
H
H H
H HHH
H
H H H
O
Functional GroupsEthers
-O-Element Grouping:
Example:
Naming: -name ends in ether
methyl propyl ether
CH2OCH3 CH2CH3
Functional GroupsHalides
Element Grouping:
Example:
Naming: -use prefix with o ending
2-chloro-3-fluoro-butane
ClCBrC
FCIC
CH3-CH-CH-CH3
Cl
F
Functional GroupsAmine
Element Grouping:
Example:
Naming: -name ends in –amine
N
NH2CH2CH2CH3
propanamine
Functional GroupsAmino Acids
Element Grouping:
Example:
Naming:
TOO complicated
OHC
O
CNH
H X
H
Functional GroupsEsters
Element Grouping:
Example:
Naming: -name ends in –oate
OC
O
CH
O
O CH2CH2CH3
propyl methanoate
Functional GroupsAmide
Element Grouping:
Example:
Naming: -name ends in –amide
methanamide
NH2C
O
NH2C
O
H
Drawing Side Chains2,2-dimethyloctane
1,3-dimethylcyclopentane
6-ethyl-5-propyl-7-methyl-1-heptene
CH3CH2CH2CH2CH2CH2-C-CH3
CH3
CH3
CH3C CH3
C
C
C
C
HH
HHH
H
H H
CH2CHCH2CH2CH2-C-CH2
CH3CH3CH2CH2
CH2CH3
BELL RINGERName the
hydrocarbon
C – C – C – O – C – C H
O
H H
H HHH
HH H
ethyl propanoate
Isomers
Structural Isomers
Butane (C4H10) 2-methylpropane (C4H10)
CH2 CH CH2 CH3 CH3 CH CH CH3
CH2 C CH3
CH3CH2
CH2
CH2
CH2
CHCH2
CH2
CH3
1-butene 2-butene
2-methylpropene cyclobutane methylcyclopropane
CH3 CH2 CH2 CH3 CH3 CH CH3
CH3
Structural Isomers
2-propanol
ethyl-methyether
CH C
H
C
HOH
H
HH
H
CH C
H
C
H OH
H
HH
H
1-propanol
CH C
H
C
H H
H
HH
H
O
Covalent Molecules Lab
BELL RINGER
Draw and name an isomer of butanal.
Generally organic reactions occur at a slower rate covalent bonds
Many reactions require a catalyst to lower the activation energy
Types of ReactionsAddition
Reactants:
Example:
Produces: -a double halogenated halocarbon
-alkene or alkyne
–C=C–
H H
HHF2
+
H
FF
HH–C–C–
H
Special Info:-only occurs with unsaturated hydrocarbons
-results in 2 atoms added
“Hydrogenation”
Helps turn oils into margarine
Special type of Addition
H–C–C–C=C–H
H H
H H
H H
+ H2H–C–C–C–C–H
H H
H H H H
H H
Types of ReactionsSubstitution
Reactants:
Example:
Produces: -a single halogenated halocarbon
saturated hydrocarbon and halogen
I2+
Special Info: -only occurs with alkanes, can add more by doing more than one substitution
H–C–C–C–C–H
H H
H H H H
H HH–C–C–C–C–H
H H
H H H I
H H
HI+
Types of ReactionsFermentation
Reactants:
Example:
Produces: Alcohol and carbon dioxide
-sugar and yeast
yeast H
OH
HH
H–C–C–
H
CO2+ 22
Types of ReactionsEsterification
Reactants:
Example:
Produces: Ester and water by
-organic acid and an alcohol
dehydration synthesis
H
–C–H
H
HO+–C – C–
H
OH
O
H
H
O
HH
H
HOH
H–C–C–O–C–H +
Types of ReactionsEsterification - DEMOS
Acetic Acid + Ethanol(ethanoic acid)
H
–C–C-H
H
HO+–C – C–
H
OH
O
H
H H
H
HOH +
O
HH
H
H–C–C–O–C–C–H
H
HH
Ethyl ethanoate + Water
Smells Like:
Fruity?
What is the name of the ester made between the reaction of
pentanol and acetic acid?
+H–C–C–
H
OH
H
O
Smells Like:
Banana?
HO
H
–C–C–C–C–C–H
H
H
H H H H
H H H
H–C–C–
H
O
H
O
H
–C–C–C–C–C–H
H
H
H H H H
H H H
+ HOH
Pentyl ethanoate
What is the name of the ester made between the reaction of methanol and salicylic acid?
Smells Like:
wintergreen
Methyl benzoate
(Methyl salicylate)
O
O
H
OH
+ HOCH3
O
O
CH3
OH
+ H2O
Types of Reactions
Saponification
Reactants:
Example:
Produces: Soap(salt of an acid) and glycerol - a fat and a strong base
Almost the reverse of esterification (hydrolysis)
Types of ReactionsCombustion (oxidation)
Reactants:
Example:
Produces: CO2 and H2O
-hydrocarbons and oxygen
CO2 H2O+
-hydrocarbons and limited O2
CO and H2O
O2+–C–C–C–
H H
HH
HH
H
H
3 45
Types of ReactionsPolymerization
Reactants:
Example:
Produces: Protein, plastics
many small molecules-amino acids, ethylene
200 C=CH H
HHC=C
H H
HH200
BELL RINGERDraw the structural formula for the
product of joining two alcohols together:
Propyl ethyl ether
BELL RINGERDraw the structural formula for the
product of joining two alcohols together:
Propyl ethyl ether
C – C – C – O – C – C H
H
H H
H HHH
H
H H H
Some additional infoSolubility
Hydrocarbons are non-polar
Alcohols and organic acids are
polar= Soluble in water
Some additional infoMP & BP
The presence of H bonds increases strength of IMF’s
Alcohols and organic acids
STRONG H Bonds
Amines
weaker H Bonds
Some additional infoSaturated vs. unsaturated
SATURATED Alkanes only
Alkenes or Alkynes
with respect to Hydrogen's
UNSATURATED
Aka ‘trans fats’ from hydrogenation
‘Trans’ fat‘Cis’ fat
Fractional Distillation
Further purification – done by cracking and polymerization
Cracking Chemical breakdown of more complex molecules into smaller ones
H. Fractional DistillationH. Fractional DistillationLighter hydrocarbons have lower melting points
CH4 C2H8 Gases at room temperature
C8H18Liquid at room temperature
Petroleum = mixture of all different hydrocarbonsHeat mixture slowly.
The different hydrocarbons are boiled to a gas and allowed to rise
As they rise, they cool off until they become liquids
Heavier hydrocarbons will not rise as high before they become liquidsLightest hydrocarbons will rise the highest
Organic Reaction Review
Compound formed Organic Reaction
Ethanol
Glycerol
Fluoroethane
Polyethylene
Dichloropropane
1. Esterification
2. Saponification
3. Polymerization
4. Fermentation
5. Substitution
6. Addition1 Methyl ethanoate
2
3
4
5
6
Bell Ringer
Examples - Perform the following reactions, identify each as addition or substitution, and draw the products
A.
B.
C.
D.
H H H | | |H--C--C--C--H | | | H H H
H H H | | |H--C--C==C--C--H | | | H H H
+ Cl2
+ Br2 + Cl2
+ F2
+ 2 I2
H |H-- C C--C--H | H
H--C C--H
H H H | | |H--C--C--C--H | | | Cl H H
+ HCl
H H Br H | | | |H--C--C--C--C--H | | | | H Br H H
Cl H Br H | | | |H--C--C--C--C--H | | | | H Br H H
+ HCl
H H \ | C == C--C--H / | | F F H
I I | | H--C--C--H | | I I
2 addition reactions
addition reaction
Notice the cis!Notice the cis!
addition reaction
Substitution reaction
Substitution reaction
Examples - Write out the products of the esterification, then write the molecular formula of the ester
O || H--C--OH
H H H H | | | |HO--C--C--C--C--H | | | | H H H H
O H || | HO--C--C--H | H
H H H O | | | H--C--C--C--H | | | H H H
O || H--C--
H H H H | | | | O--C--C--C--C--H | | | | H H H H
H O | || H--C--C-- | H
H H H | | | O--C--C--C--H | | | H H H
Butyl methanoate
Propyl ethanoate
+ H2O
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