organic chemistry chapter 22-23. organic chemistry study of carbon-based compounds carbon has 4...

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 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

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 first 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

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

2,2-Dimethyl Propane

Isomer Example

H H H H │ │ │ │HO─ C─ C─ C─ C─ H │ │ │ │ H H H H

1-Butanol

H H H H │ │ │ │H─ C─ C─O ─ C─ C─ H │ │ │ │ H H H H

Diethyl Ether

C4H10O

Isomer Example

H H O │ │ ǁ H─ C─ C─ C─ H │ │ H H

Propanal

H O H │ ǁ │H─ C─ C─ C─ H │ │ H H

Propanone

C3H6O

Isomer Example

H H O │ │ ǁ H ─ C─ C─ C─ OH │ │ H H

Propanoic Acid

H O H │ ǁ │H ─ C─ O ─ C─ C─ H │ │ H H

Methyl Ethanoate

C3H6O2