Organic Chemistry
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Transcript of Organic Chemistry
Organic Chemistry
Chapter 22-23
Organic Chemistry
Study of carbon-based compounds
Carbon has 4 valence electrons Carbon always forms 4 covalent bonds
N (3), O (2), H (1)
Carbon compounds form chains and/or rings
Hydrocarbons
Molecule or compound composed of carbon and hydrogen only
Three Main Types Alkanes, Alkenes, Alkynes
Alkanes
All single C─C bonds H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H
H H H H │ │ │ │H─ C─ C─ C─ C─ H │ │ │ │ H H H H
H H H │ │ │ H─ C─ C─ C─ H │ │ │ H H H
C5H12C4H10C3H8
General Formula CnH2n+2
Alkenes
At least one double C=C bond H H H H H │ │ │ │ │ H ─ C─ C─ C─ C= C─ H │ │ │ H H H
H H H H │ │ │ │H─ C─ C─ C= C─ H │ │ H H
H H H │ │ │ H─ C─ C= C─ H │ H
C5H10C4H8C3H6
General Formula CnH2n
Alkynes
At least one triple C≡C bonds H H H │ │ │ H ─ C─ C─ C─ C≡ C─ H │ │ │ H H H
H H │ │ H─ C─ C─ C≡ C─ H │ │ H H
H │ H─ C─ C≡ C─ H │ H
C5H8C4H6C3H4
General Formula CnH2n-2
Homologous Series
Group of compounds with similar structure and function Table Q
Members increase by one carbon and two hydrogens
Alkane Homologous Series
H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H
C5H12
H H H H │ │ │ │H─ C─ C─ C─ C─ H │ │ │ │ H H H H
C4H10
H H H │ │ │ H─ C─ C─ C─ H │ │ │ H H H
C3H8
H H │ │ H─ C─ C─ H │ │ H H
C2H6
H │ H─ C─ H │ H
CH4
H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H │ │ │ │ │ │ H H H H H H
C6H14
Alkene Homologous Series
H H H H H │ │ │ │ │ H ─ C─ C─ C─ C= C─ H │ │ │ H H H
C5H10
H H H H │ │ │ │H─ C─ C─ C= C─ H │ │ H H
C4H8
H H H │ │ │ H─ C─ C= C─ H │ H
C3H6
H H │ │ H─ C= C─ H
C2H4
H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C= C─ H │ │ │ │ H H H H
C6H12
Alkyne Homologous Series
H H H │ │ │ H ─ C─ C─ C─ C≡ C─ H │ │ │ H H H
C5H8
H H │ │ H─ C─ C─ C≡ C─ H │ │ H H
C4H6
H │ H─ C─ C≡ C─ H │ H
C3H4
H─ C≡ C─ H
C2H2
H H H H │ │ │ │ H ─ C─ C─ C─ C─ C≡ C─ H │ │ │ │ H H H H
C6H10
Saturated vs. Unsaturated
Saturated Hydrocarbons Contain only single Carbon to Carbon
bonds (Alkanes)
Unsaturated Hydrocarbons Contains at least one multiple (double,
triple) Carbon to Carbon bond Alkenes and Alkynes
Naming Simple Hydrocarbons
Name is based on two parts Number of carbons in longest
continuous chain (Table P) Type of bonds between carbons
Single –ane Double –ene Triple –yne
Examples
Butane
Pentane
H H H H │ │ │ │H─ C─ C─ C─ C─ H │ │ │ │ H H H H
H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H
Alkenes and Alkynes
Name includes location of multiple bond Carbons numbered to give multiple
bond the lowest possible number
1-butyne 2-butyne
H H │ │ H─ C─ C─ C≡ C─ H │ │ H H
H H │ │ H─ C─ C≡ C ─ C─ H │ │ H H
Chemical Formula
Shows only number of each type of element C2H6
C6H12O6
Structural Formula
Shows how each atom is bonded to each other
H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H
H H │ │ H─ C─ C─ C≡ C─ H │ │ H H
Condensed Structural Formula
Shows who is bonded to who, without the actual bonds
H H H │ │ │ H─ C─ C= C─ H │ H
H H H │ │ │ H─ C─ C─ C─ H │ │ │ H H H
323 CHCHCH 23CHCHCH
Branched Hydrocarbons
Alkyl Group Hydrocarbon branch Branch name ends with -yl Location of branch is indicated by
number Number carbons to give lowest possible
number Multiple bond still takes priority in
numbering
Examples
3-Methyl Pentane
2-Methyl 1-Butene
H H CH3 H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H
H │ H─ C─ H │ H CH2 H │ │ │ H─ C─ C= C─ H │ H
Isomers
Two or more compounds with the same chemical formulas, but different structural formulas and properties Different Names
Isomer Example
H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H H H H H
H H CH3 H │ │ │ │H─ C─ C─ C─ C─ H │ │ │ │ H H H H
Pentane Methyl Butane
C5H12
H CH3 H │ │ │ H─ C─ C─ C─ H │ │ │ H CH3 H
Dimethyl Propane
Functional Groups
Specific arrangement of atoms that give compounds a unique property Table R
Examples Hydroxyl Group, -OH O Carbonyl Group, ─ C ─
ǁ
Halides
Halogen attached to a carbon Prefix indicates which halogen
Table R # for which carbon halogen is
attached Multiple bonds still take priority in
numbering
Halides
H H Cl H │ │ │ │H─ C─ C─ C─ C─ H │ │ │ │ H H H H
2-Chlorobutane
Br H H │ │ │ H─ C─ C= C─ H │ H
3-Bromopropene
CH3CH2CHClCH3 CH2BrCHCH2
Alcohol
Hydroxyl group (-OH) attached to a carbon # for which alcohol group is attached Name ends in –ol Multiple bonds still take priority in
numbering
Alcohol
H H H H │ │ │ │HO─ C─ C─ C─ C─ H │ │ │ │ H H H H
1-Butanol 3-Hexanol
H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H │ │ │ │ │ │ H H H OH H H
CH3CH2CH2CH2OH CH3CH2CH2CHOHCH2CH3
Aldehyde
Carbonyl group at end of chain Name ends with –al Condensed structural formula ends
with -CHO
O ǁ─ C ─ H
Aldehyde
H H O │ │ ǁ H─ C─ C─ C─ H │ │ H H
Propanal
CH3CH2CHO
H H H H O │ │ │ │ ǁ H ─ C─ C─ C─ C─ C─ H │ │ │ │ H H H H
Pentanal
CH3CH2CH2CH2CHO
Ketones
Carbonyl group not on end of chain Number indicates which carbon the
oxygen is attached to Name ends with –one Condensed structural formula has -
CO- in it O ǁ─ C ─
Ketones
H O H │ ǁ │H─ C─ C─ C─ H │ │ H H
Propanone
CH3COCH3
H O H H H │ ǁ │ │ │H ─ C─ C─ C─ C─ C─ H │ │ │ │ H H H H
2-Pentanone
CH3COCH2CH2CH3
Amine
Nitrogen attached to a carbon Number indicates which carbon the
nitrogen is attached to Name ends in –amine Multiple bonds still take priority in
numbering
Amine
H H H H │ │ │ │H2N─ C─ C─ C─ C─ H │ │ │ │ H H H H
1-Butanamine 3-Hexanamine
H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H │ │ │ │ │ │ H H H NH2 H H
CH3CH2CH2CH2NH2 CH3CH2CH2CHNH2CH2CH3
Amide
Carbonyl group with an amine group attached to it Must be on an end Name ends in -amide
O H ǁ ǀ─ C ─ N ─ H
Amide
H H O │ │ ǁ H─ C─ C─ C─ NH2
│ │ H H
Propanamide
CH3CH2CONH2
H H H H O │ │ │ │ ǁ H ─ C─ C─ C─ C─ C─ NH2
│ │ │ │ H H H H
Pentanamide
CH3CH2CH2CH2CONH2
Organic Acid
Carbonyl group with a hydroxyl group attached to it Must be on an end Name ends in –oic acid Condensed structural formula ends
with -COOH Hydroxyl H is the acidic H
O ǁ ─ C ─ O ─ H
Organic Acid
H O │ ǁ H ─ C─ C─ OH │ H
Ethanoic Acid
CH3COOH
H H H O │ │ │ ǁ H ─ C─ C─ C─ C─ OH │ │ │ H H H
Butanoic Acid
CH3CH2CH2COOH
Ether
Single oxygen between 2 carbon chains
Name each carbon chain
Butyl Ethyl Ether
H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ O─ C─ C─ H │ │ │ │ │ │ H H H H H H
H H H H │ │ │ │H─ C─ C─O ─ C─ C─ H │ │ │ │ H H H H
Diethyl Ether
CH3CH2OCH2CH3CH3CH2CH2CH2OCH2CH3
Ester
Carbonyl group with single oxygen between carbon chains
Name in two parts 1st – Branch off oxygen as alkyl group 2nd – Chain containing Carbonyl group Ending in –oate
O ǁ ─ C ─ O ─
Ester
H O H │ ǁ │H ─ C─ O ─ C─ C─ H │ │ H H
Methyl Ethanoate
CH3COOCH3
Ethyl Butanoate
H H H O H H │ │ │ ǁ │ │ H ─ C─ C─ C─ C─ O─ C─ C─ H │ │ │ │ │ H H H H H
CH3CH2CH2COOCH2CH3
Organic Reactions
Saponification Fermentation Combustion Addition Substitution Polymerization (2 types) Esterification
Organic Reactions
Saponification Production of Soap
Fermentation Production of ethanol and CO2 from
sugar C6H12O6 2C2H5OH + 2CO2
Combustion
Complete Combustion of a Hydrocarbon CxHy + O2 CO2 + H2O
Example: C3H8 + 5O2 3CO2 + 4H2O
Addition
Addition of a halogen onto an alkene or alkyne
Br Br Br Br │ │ │ │ H─ C= C─ H + Cl─Cl H─ C─ C─ H
│ │ Cl Cl
Br Br │ │ H─ C≡ C─ H + Br─Br H─ C= C─ H
Substitution
Substitution of one halogen in place of a hydrogen on an alkane
H H H H │ │ │ │ H─ C─ C─ H + Cl─Cl H─ C─ C─ H + H ─ Cl │ │ │ │ H H H Cl
H H Br H │ │ │ │ H─ C─ C─ H + Br─Br H─ C─ C─ H + H ─ Br │ │ │ │ H Cl H Cl
Polymerization
Connecting of smaller pieces into a long repeating chain Plastics, starches, nylon
Two types: Addition Condensation
-(C2H4)n-
Addition Polymerization
Double or triple bonds break to connect pieces together
H H H H H H H H │ │ │ │ │ │ │ │ C═C + C═C ─ C─C─C─ C ─ │ │ │ │ │ │ │ │ H H H H H H H H
n
Condensation Polymerization
Removal of water is used to link pieces together
H H H H H H H H │ │ │ │ │ │ │ │H─O─ C─C─O─H + H─ O─ C─C─O─H H─O─C─C─O─C─C─O─H + H2O │ │ │ │ │ │ │ │ H H H H H H H H
Esterification
Production of an Ester from an alcohol and acid Alcohol + Acid Ester + Water
H O H O │ ǁ │ ǁH─ C─ O ─ H + H ─O ─C ─H H─ C─ O ─ C─ H + H2O │ │ H H