Chapter 22 23
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Chapter 22-23. Organic Chemistry. 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

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Chapter 22 23

Chapter 22-23

Organic Chemistry


Organic chemistry

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

Hydrocarbons

  • Molecule or compound composed of carbon and hydrogen only

  • Three Main Types

    • Alkanes, Alkenes, Alkynes


Alkanes

Alkanes

  • All single C─C bonds

H H H

│ │ │

H─ C─ C─ C─ H

│ │ │

H H H

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

C3H8

C4H10

C5H12

General Formula

CnH2n+2


Alkenes

Alkenes

  • At least one double C=C bond

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

Alkynes

  • At least one triple C≡C bonds

H

H─ C─ C≡ C─ H

H

H H

│ │

H─ C─ C─ C≡ C─ H

│ │

H H

H H H

│ │ │

H ─ C─ C─ C─ C≡ C─ H

│ │ │

H H H

C3H4

C4H6

C5H8

General Formula

CnH2n-2


Homologous series

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─ C─ H

H

H H

│ │

H─ C─ C─ H

│ │

H H

H H H

│ │ │

H─ C─ C─ C─ H

│ │ │

H H H

H H H H

│ │ │ │

H─ C─ C─ C─ C─ H

│ │ │ │

H H H H

CH4

C2H6

C3H8

C4H10

H H H H H

│ │ │ │ │

H ─ C─ C─ C─ C─ C─ H

│ │ │ │ │

H H H H H

H H H H H H

│ │ │ │ │ │

H ─ C─ C─ C─ C─ C─ C─ H

│ │ │ │ │ │

H H H H H H

C5H12

C6H14

Alkane Homologous Series


Alkene homologous series

H H

│ │

H─ C= C─ H

H H H

│ │ │

H─ C─ C= C─ H

H

H H H H

│ │ │ │

H─ C─ C─ C= C─ H

│ │

H H

C2H4

C3H6

C4H8

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─ C= C─ H

│ │ │ │

H H H H

C5H10

C6H12

Alkene Homologous Series


Alkyne homologous series

H─ C≡ C─ H

H

H─ C─ C≡ C─ H

H

H H

│ │

H─ C─ C─ C≡ C─ H

│ │

H H

C2H2

C3H4

C4H6

H H H

│ │ │

H ─ C─ C─ C─ C≡ C─ H

│ │ │

H H H

H H H H

│ │ │ │

H ─ C─ C─ C─ C─ C≡ C─ H

│ │ │ │

H H H H

C5H8

C6H10

Alkyne Homologous Series


Saturated vs unsaturated

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

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

Examples

H H H H

│ │ │ │

H─ C─ C─ C─ C─ H

│ │ │ │

H H H H

  • Butane

  • Pentane

H H H H H

│ │ │ │ │

H ─ C─ C─ C─ C─ C─ H

│ │ │ │ │

H H H H H


Alkenes and alkynes

Alkenes and Alkynes

  • Name includes location of multiple bond

    • Carbons numbered to give multiple bond the lowest possible number

    • 1-butyne2-butyne

H H

│ │

H─ C─ C─ C≡ C─ H

│ │

H H

H H

│ │

H─ C─ C≡ C ─ C─ H

│ │

H H


Chemical formula

Chemical Formula

  • Shows only number of each type of element

    • C2H6

    • C6H12O6


Structural formula

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

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 H

│ │ │

H─ C─ C= C─ H

H


Branched hydrocarbons

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


Examples1

Examples

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

H


Isomers

Isomers

  • Two or more compounds with the same chemical formulas, but different structural formulas and properties

    • Different Names


Isomer example

Isomer Example

C5H12

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

H CH3 H

│ │ │

H─ C─ C─ C─ H

│ │ │

H CH3 H

Dimethyl Propane


Functional groups

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


Halides1

Halides

H H Cl 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


Alcohol1

Alcohol

H H H H

│ │ │ │

HO─ C─ C─ C─ C─ H

│ │ │ │

H H H H

H H H H H H

│ │ │ │ │ │

H ─ C─ C─ C─ C─ C─ C─ H

│ │ │ │ │ │

H H H OH H H

3-Hexanol

1-Butanol

CH3CH2CH2CH2OH

CH3CH2CH2CHOHCH2CH3


Aldehyde

Carbonyl group at end of chain

Name ends with –al

Condensed structural formula ends with -CHO

Aldehyde

O

ǁ

─ C ─ H


Aldehyde1

Aldehyde

H H H H O

│ │ │ │ ǁ

H ─ C─ C─ C─ C─ C─ H

│ │ │ │

H H H H

H H O

│ │ ǁ

H─ C─ C─ C─ H

│ │

H H

Propanal

Pentanal

CH3CH2CHO

CH3CH2CH2CH2CHO


Ketones

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 ─


Ketones1

Ketones

H O H H H

│ ǁ │ │ │

H ─ C─ C─ C─ C─ C─ H

│ │ │ │

H H H H

H O H

│ ǁ │

H─ C─ C─ C─ H

│ │

H H

Propanone

2-Pentanone

CH3COCH3

CH3COCH2CH2CH3


Amine

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


Amine1

Amine

H H H H

│ │ │ │

H2N─ C─ C─ C─ C─ H

│ │ │ │

H H H H

H H H H H H

│ │ │ │ │ │

H ─ C─ C─ C─ C─ C─ C─ H

│ │ │ │ │ │

H H H NH2 H H

3-Hexanamine

1-Butanamine

CH3CH2CH2CH2NH2

CH3CH2CH2CHNH2CH2CH3


Amide

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


Amide1

Amide

H H H H O

│ │ │ │ ǁ

H ─ C─ C─ C─ C─ C─ NH2

│ │ │ │

H H H H

H H O

│ │ ǁ

H─ C─ C─ C─ NH2

│ │

H H

Propanamide

Pentanamide

CH3CH2CONH2

CH3CH2CH2CH2CONH2


Organic acid

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 acid1

Organic Acid

H H H O

│ │ │ ǁ

H ─ C─ C─ C─ C─ OH

│ │ │

H H H

H O

│ ǁ

H ─ C─ C─ OH

H

Ethanoic Acid

Butanoic Acid

CH3COOH

CH3CH2CH2COOH


Ether

Ether

  • Single oxygen between 2 carbon chains

  • Name each carbon chain

H H H H

│ │ │ │

H─ C─ C─O ─ C─ C─ H

│ │ │ │

H H H H

H H H H H H

│ │ │ │ │ │

H ─ C─ C─ C─ C─ O─ C─ C─ H

│ │ │ │ │ │

H H H H H H

Diethyl Ether

Butyl Ethyl Ether

CH3CH2OCH2CH3

CH3CH2CH2CH2OCH2CH3


Ester

O

ǁ

─ C ─ O ─

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


Ester1

Ester

H O H

│ 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

Organic Reactions

  • Saponification

  • Fermentation

  • Combustion

  • Addition

  • Substitution

  • Polymerization (2 types)

  • Esterification


Organic reactions1

Organic Reactions

  • Saponification

    • Production of Soap

  • Fermentation

    • Production of ethanol and CO2 from sugar

    • C6H12O6 2C2H5OH + 2CO2


Combustion

Combustion

  • Complete Combustion of a Hydrocarbon

    • CxHy + O2 CO2 + H2O

  • Example:

    • C3H8 + 5O2 3CO2 + 4H2O


Addition

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

  • 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

Polymerization

  • Connecting of smaller pieces into a long repeating chain

    • Plastics, starches, nylon

  • Two types:

    • Addition

    • Condensation

-(C2H4)n-


Addition polymerization

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

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

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


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