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Organic Chemistry
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Organic Chemistry

Jan 04, 2016

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Page 1: Organic Chemistry

Organic Chemistry

Page 2: Organic Chemistry

BELL RINGER

What makes a compound

organic?

Page 3: Organic Chemistry

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

Page 4: Organic Chemistry

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…

Page 5: Organic Chemistry

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

Page 6: Organic Chemistry

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

Page 7: Organic Chemistry

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

Page 8: Organic Chemistry

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

Page 9: Organic Chemistry

Naming Hydrocarbons (nomenclature)

Page 10: Organic Chemistry

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

Page 11: Organic Chemistry

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

Page 12: Organic Chemistry

BELL RINGER

What is the structural formula for 2-hexene

CH3CHCHCH2CH2CH3

Page 13: Organic Chemistry

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

Page 14: Organic Chemistry

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

Page 15: Organic Chemistry

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

Page 16: Organic Chemistry

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)

Page 17: Organic Chemistry

-ane

Naming side chains

CH3 CH2 CH

CH3

CH2 C

CH2

CH3

CH3

CH3

Rule 1: choose the correct ending

Page 18: Organic Chemistry

ane

Rule 2: longest carbon chain

Naming side chains

CH3 CH2 CH

CH3

CH2 C

CH2

CH3

CH3

CH3

Page 19: Organic Chemistry

aneHeptane

Rule 3: attach prefix (according to # of C)

Naming side chains

CH3 CH2 CH

CH3

CH2 C

CH2

CH3

CH3

CH3

Page 20: Organic Chemistry

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

Page 21: Organic Chemistry

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

Page 22: Organic Chemistry

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

Page 23: Organic Chemistry

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

Page 24: Organic Chemistry

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

Page 25: Organic Chemistry

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

Page 26: Organic Chemistry

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

Page 27: Organic Chemistry

Functional GroupsAlcohols

-OHElement Grouping:

Example:

Naming: -name ends in –ol

CHCH2CH3 CH3

OH

2-butanol

Page 28: Organic Chemistry

Functional GroupsAlcohols

Ethylene glycol 1,2 Ethanediol

CHO C

H

OH

H

H H

Odorless, colorless, sweet and syrupy, toxic liquid

                                      

Page 29: Organic Chemistry

Functional GroupsAldehydes

Element Grouping:

Example:

Naming: -name ends in –al

ethanal

C

O

H

CH3 C

O

H

Page 30: Organic Chemistry

Functional GroupsKetones

Element Grouping:

Example:

Naming: -name ends in –one

propanone

C

O

CH3 C CH3

O

Page 31: Organic Chemistry

Functional GroupsOrganic Acids

Element Grouping:

Example:

Naming: -name ends in –oic acid

butanoic acid

OHC

O

CH2CH2CH3 C

O

OH

Page 32: Organic Chemistry

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

Page 33: Organic Chemistry

Functional GroupsEthers

-O-Element Grouping:

Example:

Naming: -name ends in ether

methyl propyl ether

CH2OCH3 CH2CH3

Page 34: Organic Chemistry

Functional GroupsHalides

Element Grouping:

Example:

Naming: -use prefix with o ending

2-chloro-3-fluoro-butane

ClCBrC

FCIC

CH3-CH-CH-CH3

Cl

F

Page 35: Organic Chemistry

Functional GroupsAmine

Element Grouping:

Example:

Naming: -name ends in –amine

N

NH2CH2CH2CH3

propanamine

Page 36: Organic Chemistry

Functional GroupsAmino Acids

Element Grouping:

Example:

Naming:

TOO complicated

OHC

O

CNH

H X

H

Page 37: Organic Chemistry

Functional GroupsEsters

Element Grouping:

Example:

Naming: -name ends in –oate

OC

O

CH

O

O CH2CH2CH3

propyl methanoate

Page 38: Organic Chemistry

Functional GroupsAmide

Element Grouping:

Example:

Naming: -name ends in –amide

methanamide

NH2C

O

NH2C

O

H

Page 39: Organic Chemistry

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

Page 40: Organic Chemistry

BELL RINGERName the

hydrocarbon

C – C – C – O – C – C H

O

H H

H HHH

HH H

ethyl propanoate

Page 41: Organic Chemistry

Isomers

Page 42: Organic Chemistry

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

Page 43: Organic Chemistry

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

Page 44: Organic Chemistry

Covalent Molecules Lab

Page 45: Organic Chemistry

BELL RINGER

Draw and name an isomer of butanal.

Page 46: Organic Chemistry

Generally organic reactions occur at a slower rate covalent bonds

Many reactions require a catalyst to lower the activation energy

Page 47: Organic Chemistry

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

Page 48: Organic Chemistry

“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

                                                                            

Page 49: Organic Chemistry

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+

Page 50: Organic Chemistry

Types of ReactionsFermentation

Reactants:

Example:

Produces: Alcohol and carbon dioxide

-sugar and yeast

yeast H

OH

HH

H–C–C–

H

CO2+ 22

Page 51: Organic Chemistry

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 +

Page 52: Organic Chemistry

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?

Page 53: Organic Chemistry

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

Page 54: Organic Chemistry

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

Page 55: Organic Chemistry

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)

Page 56: Organic Chemistry

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

Page 57: Organic Chemistry

Types of ReactionsPolymerization

Reactants:

Example:

Produces: Protein, plastics

many small molecules-amino acids, ethylene

200 C=CH H

HHC=C

H H

HH200

Page 58: Organic Chemistry

BELL RINGERDraw the structural formula for the

product of joining two alcohols together:

Propyl ethyl ether

Page 59: Organic Chemistry

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

Page 60: Organic Chemistry

Some additional infoSolubility

Hydrocarbons are non-polar

Alcohols and organic acids are

polar= Soluble in water

Page 61: Organic Chemistry

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

Page 62: Organic Chemistry

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

Page 63: Organic Chemistry

Fractional Distillation

Further purification – done by cracking and polymerization

Cracking Chemical breakdown of more complex molecules into smaller ones

Page 64: Organic Chemistry

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

Page 65: Organic Chemistry
Page 66: Organic Chemistry

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

Page 67: Organic Chemistry

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

Page 68: Organic Chemistry

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