Organic Chemistry Chapter 22-23

Organic Chemistry Study of carbon-based compounds Carbon has 4 valence electrons Carbon always forms 4 covalent bonds 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 General Formula CnH2n+2 C3H8 C4H10 C5H12 H H H │ │ │ H─ C─ C─ C─ H H H H H │ │ │ │ H─ C─ C─ C─ C─ H H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H C3H8 C4H10 C5H12 General Formula CnH2n+2

Alkenes At least one double C=C bond General Formula CnH2n C3H6 C4H8 H H H │ │ │ H─ C─ C= C─ H │ H H H H H │ │ │ │ H─ C─ C─ C= C─ H │ │ H H H H H H H │ │ │ │ │ H ─ C─ C─ C─ C= C─ H │ │ │ H H H C3H6 C4H8 C5H10 General Formula CnH2n

Alkynes At least one triple C≡C bonds General Formula CnH2n-2 C3H4 │ H─ C─ C≡ C─ H H H │ │ H─ C─ C─ C≡ C─ H H H H │ │ │ H ─ C─ C─ C─ C≡ C─ H C3H4 C4H6 C5H8 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─ C─ H CH4 H H │ │ H─ C─ C─ H C2H6 H H H │ │ │ H─ C─ C─ C─ H C3H8 H H H H │ │ │ │ H─ C─ C─ C─ C─ H C4H10 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H C5H12 H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H C6H14

Alkene Homologous Series H H │ │ H─ C= C─ H C2H4 H H H │ │ │ H─ C─ C= C─ H │ H C3H6 H H H H │ │ │ │ H─ C─ C─ C= C─ H │ │ H H C4H8 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C= C─ H │ │ │ H H H C5H10 H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C= C─ H │ │ │ │ H H H H C6H12

Alkyne Homologous Series H─ C≡ C─ H C2H2 H │ H─ C─ C≡ C─ H C3H4 H H │ │ H─ C─ C─ C≡ C─ H C4H6 H H H │ │ │ H ─ C─ C─ C─ C≡ C─ H C5H8 H H H H │ │ │ │ H ─ C─ C─ C─ C─ C≡ C─ 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─ C─ C─ C─ C─ H Butane Pentane H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ 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─ C─ C≡ C ─ C─ 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─ C─ C─ C≡ C─ 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─ C─ C= C─ H │ H

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 3-Methyl Pentane 2-Methyl 1-Butene H │ H─ C─ H H CH2 H │ │ │ H─ C─ C= C─ H

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 Br H H │ │ │ │ │ │ │ H─ C─ C─ C─ C─ H H H H H Br H H │ │ │ H─ C─ C= C─ H │ H 2-Chlorobutane 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 H H │ │ │ │ │ │ │ │ │ │ HO─ C─ C─ C─ C─ H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H H H H OH H H 1-Butanol 3-Hexanol CH3CH2CH2CH2OH CH3CH2CH2CHOHCH2CH3

Aldehyde Carbonyl group at end of chain O ǁ ─ C ─ H 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 H H H H O │ │ │ │ ǁ │ │ ǁ H─ C─ C─ C─ H │ │ H H H H H H O │ │ │ │ ǁ H ─ C─ C─ C─ C─ C─ H │ │ │ │ H H H H Propanal Pentanal CH3CH2CHO CH3CH2CH2CH2CHO

Ketones Carbonyl group not on end of chain O ǁ ─ C ─ 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 H O H H H │ ǁ │ │ │ │ ǁ │ H─ C─ C─ C─ H │ │ H H H O H H H │ ǁ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ H H H H Propanone 2-Pentanone CH3COCH3 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 H H │ │ │ │ │ │ │ │ │ │ H2N─ C─ C─ C─ C─ H H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ C─ C─ H H H H NH2 H H 1-Butanamine 3-Hexanamine CH3CH2CH2CH2NH2 CH3CH2CH2CHNH2CH2CH3

Amide Carbonyl group with an amine group attached to it O H ǁ ǀ 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 H H H H O │ │ │ │ ǁ │ │ ǁ H─ C─ C─ C─ NH2 │ │ H H H H H H O │ │ │ │ ǁ H ─ C─ C─ C─ C─ C─ NH2 │ │ │ │ H H H H Propanamide Pentanamide CH3CH2CONH2 CH3CH2CH2CH2CONH2

Organic Acid O ǁ ─ C ─ O ─ H 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

Organic Acid H O │ ǁ H ─ C─ C─ OH │ H H H H O │ │ │ ǁ │ ǁ H ─ C─ C─ OH │ H H H H O │ │ │ ǁ H ─ C─ C─ C─ C─ OH │ │ │ H H H Ethanoic Acid Butanoic Acid CH3COOH CH3CH2CH2COOH

Ether Single oxygen between 2 carbon chains Name each carbon chain H H H H H H │ │ │ │ │ │ H ─ C─ C─ C─ C─ O─ C─ C─ H H H H H │ │ │ │ H─ C─ C─O ─ C─ C─ H Butyl Ethyl Ether Diethyl Ether CH3CH2CH2CH2OCH2CH3 CH3CH2OCH2CH3

O ǁ ─ C ─ O ─ Ester Carbonyl group with single oxygen between carbon chains Name in two parts 1st Branch off oxygen first as alkyl group 2nd Chain containing Carbonyl group Ending in –oate

Ester H O H │ ǁ │ H ─ C─ O ─ C─ C─ H │ │ H H H H H O H H │ │ │ ǁ │ │ │ ǁ │ H ─ C─ O ─ C─ C─ H │ │ H H H H H O H H │ │ │ ǁ │ │ H ─ C─ C─ C─ C─ O─ C─ C─ H │ │ │ │ │ H H H H H Methyl Ethanoate Ethyl Butanoate CH3COOCH3 CH3CH2CH2COOCH2CH3

Organic Reactions Saponification Fermentation Combustion Addition Substitution Polymerization (2 types) Esterification

Organic Reactions Saponification Fermentation Production of Soap Production of ethanol and CO2 from sugar C6H12O6  2C2H5OH + 2CO2

Combustion Complete Combustion of a Hydrocarbon Example: CxHy + O2  CO2 + H2O Example: C3H8 + 5O2  3CO2 + 4H2O

Addition Addition of a halogen onto an alkene or alkyne Br Br │ │ │ │ H─ C≡ C─ H + Br─Br  H─ C= C─ H Br Br Br Br │ │ │ │ H─ C= C─ H + Cl─Cl  H─ C─ C─ H │ │ Cl Cl

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 -(C2H4)n- 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 n H H H H H H H H │ │ │ │ │ │ │ │ C═C + C═C  ─ C─C─C─ C ─ │ │ │ │ │ │ │ │ H H H H H H H H

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 │ ǁ H─ C─ O ─ H + H ─O ─C ─H  H─ C─ O ─ C─ H + H2O │ │ H H

Isomers Two or more compounds with the same chemical formulas, but different structural formulas and properties Different Names

Isomer Example C5H12 H H H H H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H │ │ │ │ │ H ─ C─ C─ C─ C─ C─ H H H CH3 H │ │ │ │ H─ C─ C─ C─ C─ H H H H H Pentane Methyl Butane H CH3 H │ │ │ H─ C─ C─ C─ H 2,2-Dimethyl Propane

Isomer Example C4H10O H H H H │ │ │ │ HO─ C─ C─ C─ C─ H H H H H │ │ │ │ HO─ C─ C─ C─ C─ H H H H H │ │ │ │ H─ C─ C─O ─ C─ C─ H 1-Butanol Diethyl Ether

Isomer Example C3H6O H H O │ │ ǁ H─ C─ C─ C─ H │ │ H H H O H │ ǁ │ │ │ ǁ H─ C─ C─ C─ H │ │ H H H O H │ ǁ │ H─ C─ C─ C─ H │ │ H H Propanal Propanone

Isomer Example C3H6O2 H O H H H O │ ǁ │ │ │ ǁ H ─ C─ O ─ C─ C─ H │ ǁ │ H ─ C─ O ─ C─ C─ H │ │ H H H H O │ │ ǁ H ─ C─ C─ C─ OH │ │ H H Propanoic Acid Methyl Ethanoate