Organic Chemistry

The Chemistry of Carbon

Table of Contents‘Organic Chemistry’

Distilling Crude Oil Methane Ethane Propane Butane PentaneAlkanesAlcoholsAldehydes and KetonesEthersFunctional Groups

Alkenes & AlkynesCycloalkanesBenzeneAromatic HydrocarbonsCarboxylic AcidsClasses of Organic

CompoundsChiralityPolymers

Organic Chemistry

Organic Chemistry: The chemistry of carbon and carbon-based compounds

Organic Chemistry in everyday life:

Smells & tastes: fruits, chocolate, fish, mint

Medications: aspirin, Tylenol, decongestants, sedatives

Addictive substances: caffeine, nicotine, alcohol, narcotics

Hormones/Neurotransmitters: adrenaline, epinephrine

Food: carbohydrates, protein, fat

Genetics: DNA, RNA

Consumer products: plastics, nylon, rayon, polyester

Friedrich Wöhler

Made the first organic compound fromnon-living substances. Shot down theVital Force idea of organic substances.

Distilling Crude Oil

Fractional Distillation

of Crude Oil

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 429

Energy Sources in United States

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 648

Wood Coal Petroleum / natural gas Hydro and nuclear

1850

100

80

60

40

20

0

Per

cent

9

91

1900

21

71

5 3

1940

10

50

40

1980

20

70

10

1990

26

58

16

Distilling Crude Oil

Separate fractionsbased on differences in boiling point.

American Petroleum UsageAMERICAN PETROLEUM USAGE

1 Barrel of Petroleum 93% Energy Marketplace

7% Materials Marketplace

42 Gallons of Crude Petroleum 36 Gallons Fuel

36 Gallons Fuel 19 Gallons Gasoline(11 Gallons in 1920)

At $3.00 per gallon $108.00

7% (3 Gallons Crude) 100 Nylon Shirts

At $20.00 per shirt $2000.00

Entrepreneurs:

[Put an alligator on the shirt and make even more $$$$$]

A Lesson in Economics

(42 gallons)

OR

London Dispersion Forces

The temporary separations of charge that lead to the London force attractions are what attract one nonpolar molecule to its neighbors.

Fritz London1900-1954

London forces increase with the size of the molecules.

Boiling points of simplehydrocarbons in degrees Kelvin

C5H12

C4H10

C3H8

C2H6

CH4

C8H18

Molecular Weight

50 100 150

50

100

150

200

250

300

350

400

Tem

pera

ture

(Kel

vin)

London Forces in Hydrocarbons

Boiling points of simplehydrocarbons in degrees Kelvin

C5H12

C4H10

C3H8

C2H6

CH4

Simple hydrocarbons haveonly London dispersionforces as intermolecular forces

C8H18

Molecular Weight50 100 150

50

100

150

200

250

300

350

400

molecular formula

structural formula

molecular shape

ball-and-stick model

CH4 C

H

H

HH

H

H

H

H

109.5o

C

tetrahedrontetrahedralshape ofmethane

CH

H

H

H

Methane is Tetrahedral

H

H

H

H

C

Methane is Tetrahedral

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 634

Methane

molecular formula

structural formula

molecular shape

ball-and-stick model

CH4 C

H

H

HH

H

H

H

H

109.5o

C

Methane

Timberlake, Chemistry 7th Edition, page 365

tetrahedron

ball-and-stickmodel of methane

tetrahedralshape ofmethane

CH

H

H

H

H

C C H

H

HH

H

Lewis structure of Ethane

Space filling model of Ethane

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

Ball and Stick model of Ethane

Structure of Propane

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

Structure of Butane

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 635

Ball and Stick Models

Ethane C2H6 Propane C3H8

Timberlake, Chemistry 7th Edition, page 366

First Ten HydrocarbonsName

Methane

Ethane

Propane

Butane

Pentane

Hexane

Heptane

Octane

Nonane

Decane

1

2

3

4

5

6

7

8

9

10

CH4

C2H6

C3H8

C4H10

C5H12

C6H14

C7H16

C8H18

C9H20

C10H22

CH4

CH3CH3

CH3CH2CH3

CH3CH2CH2CH3

CH3CH2CH2CH2CH3

CH3CH2CH2CH2CH2CH3

CH3CH2CH2CH2CH2CH2CH3

CH3CH2CH2CH2CH2CH2CH2CH3

CH3CH2CH2CH2CH2CH2CH2CH2CH3

CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

Number ofCarbon Atoms

Molecular Formula

Condensed StructuralFormula

Hydrocarbons (alkanes)

First Ten HydrocarbonsName

Methane

Ethane

n-Propane

n-Butane

n-Pentane

n-Hexane

n-Heptane

n-Octane

n-Nonane

n-Decane

1

2

3

4

5

6

7

8

9

10

CH4

C2H6

C3H8

C4H10

C5H12

C6H14

C7H16

C8H18

C9H20

C10H22

Number ofCarbon Atoms

Molecular Formula

Melting Point, oC

# of Isomers

Boiling Point, oC

-182.5

-183.2

-187.7

-138.3

-129.7

- 95.3

- 90.6

- 56.8

- 53.6

- 29.7

-161.5

-88.6

-42.1

-0.5

36.1

68.7

98.4

125.7

150.8

174.0

0

0

0

2

3

5

9

18

35

75

Increasing mass and boiling point

Methane16 g/mol-161.5oC

Ethane30 g/mol-88.6oC

Propane44 g/mol-42.1oC

n-Butane58 g/mol-0.5oC

Hydrocarbons

1

2

3

4

5

6

7

8

9

10

Number ofCarbon Atoms

AlkanesCnH2n + 2

AlkynesCnH2n-2

AlkenesCnH2n

_______

Ethyne

Propyne

Butyne

Pentyne

Hexyne

Heptyne

Octyne

Nonyne

Decyne

____

C2H2

C3H4

C4H6

C5H8

C6H10

C7H12

C8H14

C9H16

C10H18

Methane

Ethane

Propane

Butane

Pentane

Hexane

Heptane

Octane

Nonane

Decane

CH4

C2H6

C3H8

C4H10

C5H12

C6H14

C7H16

C8H18

C9H20

C10H22

_______

Ethene

Propene

Butene

Pentene

Hexene

Heptene

Octene

Nonene

Decene

____

C2H4

C3H6

C4H8

C5H10

C6H12

C7H14

C8H16

C9H18

C10H20

Isomers

The fat dog shook himself, and then rolled over on the wet rug.

The dog shook the fat rug, then rolled over and wet on himself.

(These two statements use the same words...but have very different meanings.)

C H

H

H

H

Methane CH4

H

CC C C

H H H

H

HHHH

H

Butane C4H10

Butyl -C4H9

Methyl-CH3

C H

H

H

?R

H

CC C C

H H H

H

HHHH

R

Naming Alkanes1. Find the longest continuous chain of carbon atoms in the molecule

2. Start numbering the chain at the carbon nearer the first branching point (the substituents should have the lowest numbers possible)3. Name and number the substituents

If there are two substituents attached to the same carbon,assign both of them the same number

4. Write out the name of the molecule• List the substitutents names in alphabetical order if there are two identical substituents on the molecule, use the prefix di; if there are three identical substituents, use the prefix tri-; if there are four identical substituents, use the prefix tetra- (alphabetize the substituents by the main name of the substituent, not by any prefixes the substituents may have)• Separate the substituents names with hyphens• Tag the name of the parent chain onto the end of the substituent names

A Few Extra Rules to FollowUse commas to separate numbers

Use hyphens to separate numbers from the substituent names

Never name alkanes after drinking

Don’t allow children to name alkanes unattended

Butane

Butane Gas– lighters

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 107

H - C - C - C - C - H

H H H H

H H H H

Butane: C4H10

Structural Isomers of C4H10

Isomers of Butane

Timberlake, Chemistry 7th Edition, page 383

H

CC C C

H H H

H

HHHH

H

C4H10

butane

propane or isobutane H

C

C C C

H H

H

HHH

HH

H

methyl

but-1-ene

cis-but-2-ene

trans-but-2-ene

2-methylpropene

IUPAC name

C4H8

Isomers of PentaneC5H12

Timberlake, Chemistry 7th Edition, page 385

These are called structural isomers.

H

CC C C

H H H

H

HHHH

H

Butane C4H10

Butane C4H8

HCC C C

H H

H

HHHH

1-butene but(1)ene

n-butene

2-butene

1 2 3 4

CC C

H

H

HHH

H

C

H

H1 2 3 4

Butene C4H8

H C

C C C

H

H

CH3

CH3HH

H

C

C

H

H

H

H

H

hexane3, 3 dimethyl

1 2 3

4

5

6

or

1

2

3

456

hexane4, 4 dimethyl

CC C C

CH3

CC

CH3

Lowest sum of numbers is correct

CC C C

C

C

CCH3

CH3CHCH2CHCH3

CH3

H

H

H

H

H H HH

H H H

H

HH

H

H

C7H16

H

CC C C

H H H

H

HHHH

H CC C

H H H

HHH

Heptane

2, 4-dimethyl pentane

condensed structural formula

shorthand

molecular formula

HCC C C

H H HH

HHHH

H CC C

H H H

HHHCH

HH

CH

HC

H

CH

H

HCC C

HHH

CH

H

H CC C

Br

H H

Cl

Cl

HC H

H

H CC C

H H

HHH

CH

HH

2 - methylbutanebutane

CH

H

HCC C

HHH

CH

H

1, 4 - pentadiene

HH CC C

Cl

H

3 - chloro 1 - propyne

H CC C

Br

H H

Cl

Cl

3 - bromo, 1,1 -dichloro 1 - propene

Recall: double bond is lowest numbermust put substituents in alphabetical order

Naming Branched Alkanes (IUPAC)

1. Root name: name of longest continuous C chain (parent chain)Two equally long? Choose the one with more branches

2. Number C atoms in chain, starting at end with first branch

3. Identify substituents, give each a number (C it is connected to)Two or more identical substituents: use prefixes (di-, tri-, tetra-, etc.)

4. List substituents alphabetically before root nameDo not alphabetize prefixes

5. Punctuation: commas separate numbers from each otherhyphens separate numbers from namesno space between last substituent & root name

4-ethyl-3,5-dimethyloctane1

2

3

658

74

4-ethyl

3-methyl and 5-methyl = 3,5-dimethyl

Octane

Structural Isomers: Pentane (C5H12)

pentane

2-methylbutane

2,2-dimethylpropane

Structural Isomers: Hexane (C6H14)

hexane

2-methylpentane

3-methylpentane

2,3-dimethylbutane

2,2-dimethylbutane

Structural Isomers: Heptane (C7H16)

heptane

2-methylhexane

3-methylhexane

2,2-dimethylpentane

2,3-dimethylpentane

Structural Isomers: Heptane C7H16

2,4-dimethylpentane

3,3-dimethylpentane

3-ethylpentane

2,2,3-trimethylbutane

Comparing Structural IsomersC5H12

(Same formula, different structure)

More branching → weaker London dispersion forces

36.0pentane

27.92-methylbutane

9.52,2-dimethylpropane

Boiling point (°C)NameStructure

BP/MP of Linear alkanes > BP/MP of branched alkanes

Naming Alkanes Problem Set

1.

2-methylbutane

2.

3. 4.

2-methylbutane

2,3-dimethylbutane 3,3,4-trimethylhexane

Naming Alkanes Problem Set

5. 3-ethyl-2,4,5-trimethylheptane

6. 6-ethyl-2,7-dimethylnonane

Naming Alkanes Problem Set

7.

2,3,4-trimethylhexane

8.

9. 10.

4-ethyl-3-methylheptane

3,3,4-trimethylhexane 5-tert-butyl-4-isopropyl-3-methyloctane

Naming Alkanes Problem Set

11. 2,2,3-trimethylheptane

12. 6-ethyl-2-methyl-5-propylnonane

Naming Alkanes Problem Set

13.

3,5-dimethyl-4-propylheptane

14.

15. 16.

3,4,4-trimethylheptane

3-ethyl-2,2,3-trimethylpentane

4-ethyl-6-isobutyl-2,9-dimethyldecane

Naming Alkanes Problem Set17. 1,1,6-trimethylhexane

18. 2-tert-butyl-4-ethyl-3-isopropylpentane

12

3

4

5

6

78

6

1

23

45

7

2-methyloctane

4-isopropyl-2,2,3,5-tetramethylheptane

Naming Alkanes Problem Set19. 1-sec-butyl-4-isobutyl-3-methylbutane

20. 4,5,5-trimethylhexane

12 3

4

5

6

7

2,5,8-trimethyldecane

2,2,3-trimethylhexane

12

3

45

6

78

9

10

HCC C C

H HH

HHH

H CC C

H H H

HHH

CH

HH

C HH

C HH

H

3,4-dimethyl octane

CH3

CH3C CH2

Cl

CH3C C

Cl

H

3, 4 - dichloro 4 - methyl 2 - hexene

Functional GroupsHydrocarbons in which some hydrogen atoms have been replaced can be compared to an electric drill with attachments.

Inferring: What determines the function of the drill, the drill itself or the attachments?

Forstnerdrill bit

Philipsscrewdriver bit

drum sander

Twistdrill bit

hole saw bitElectric drill

Alcohols (R-OH)

R = -CH3 ‘methyl’R = -CH2CH3 ‘ethyl’

Methanol

(methyl alcohol)

Ethanol

(ethyl alcohol)

Timberlake, Chemistry 7th Edition, page 437

Primary, Secondary, Tertiary Alcohols

Primary (1o)Alcohol

Secondary (2o)Alcohol

Tertiary (3o)Alcohol

(One alkyl group) (Two alkyl groups) (Three alkyl groups)

Examples:

R1 OH

H

H

C R1 OH

H

R2

C R1 OH

R3

R2

C

CH3 OH

H

H

C CH3 OH

H

CH3

C CH3 OH

CH3

CH3

C

Carbon attachedto OH group

Alkylgroup

1o 2o 3o

Aldehydes and Ketones

Formaldehyde

(CH2O)

Acetaldehyde

(CH3CH) Acetone

(CH3COCH3)

Aldehyde R-C-H

Ketone R-C-R'

Timberlake, Chemistry 7th Edition, page 453

dimethyl ketone, 2-propanone

methanal

ethanal, ethyl aldehyde

O

O

O

Dimethyl Ether

Dimethyl ether

– C2H6O– Flammable– anesthesia

Timberlake, Chemistry 7th Edition, page 446

R- Functional Groups

-CH3

-CH2CH3

-CH2CH2CH2CH3methyl

ethyl

propyl

butyl

-CH2CH2CH3

CH3CHCH2CH3

Hsec-butyl

– CH2 – C – CH3

H

CH3

isobutyl

– C – CH3

CH3

CH3

tert-butyl

CH3CCH3

Hisopropyl

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 642

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 660

Ball and stick model of Ethylene

Zumdahl, Zumdahl, DeCoste, World of Chemistry 2002, page 651

Space filling model of Ethylene

Alkenes and Alkynes

Alkene– Double bonds

Alkynes– Triple bonds

Timberlake, Chemistry 7th Edition, page 409

A ball-and-stick model of ethene C2H4, the simplest alkene.

ethene

A ball-and-stick model of acetylene (IUPAC name ethyne)

ethyne (acetylene)

Saturated vs. Unsaturated Hydrocarbons

Saturated– Single bonds

Example:

Unsaturated– Double & triple bonds

Example:

Aliphatic Hydrocarbons

Alkane Alkene Alkyne AlkadieneGeneralformula

Typicalstructuralformula

Carbon-carbonbond type

Namingsuffix

all single bonds one double bond one triple bond two double bonds

-ane -ene -yne -diene

CnH2n + 2 CnH2n CnH2n - 2 CnH2n - 2

1-butenebutane 1-butyne 1,3-butadiene

– C = C – C – C – – C – C – C – C – – C = C – C = C – – C = C – C – C –

Hydrogenation

vegetable oils

+ H2

shortening stick margarine

tub (soft)margarine

unsaturated saturated

(an addition reaction)

Cycloalkanes

FormulaCnH2n

Cyclopropane

Cyclobutane

Cyclopentane

Cyclohexane

Condensed Structural Formula

GeometricFormula Name

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2 CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

Cycloalkanes

FormulaCnH2n

Timberlake, Chemistry 7th Edition, page 388

Cyclopropane

Cyclobutane

Cyclopentane

Cyclohexane

Condensed Structural Formula

GeometricFormula Name

Benzene

An Aromatic Compound– C6H6 – Resonance structures– Kekule’s dream

Benzene

Resonance in Benzene

Kelter, Carr, Scott, Chemistry A World d of Choices 1999, page 212

Shorthand notation of Benzene

Structure of Benzene

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

C C

C C

C C

H H

H H

H H

Structure of Benzene

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

C C

C C

C C

H H

H H

H H

Structure of Benzene

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

C C

C C

C C

H H

H H

H H

C C

C C

C C

H H

H H

H H

Benzene

3-D – VSEPR Diagram

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

Names of monosubstituted benzene rings

Cl

Br

NO2

CH3

OH

CH=CH2

Chlorobenzene

Bromobenzene

Nitrobenzene

Toluene

Phenol

Styrene

Benzene NO3- Nitrobenzene

Mark Wirtz, Edward Ehrat, David L. Cedeno*

Aromatic Hydrocarbons

Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430

Cholesterol Compounds

C C

C C

C C

CH3

ortho

position number name 1, 2 ortho- (o-) 1,3 meta- (m-) 1,4 para- (p-)

1

2

34

5

6

metapara

C C

C C

C C

H CH3

H H

H CH3

ortho-dimethylbenzeneor

1, 2 - dimethylbenzene

1

2

34

5

6

C C

C C

C C

H CH3

H CH3

H H

meta-dimethylbenzeneor

1, 3 - dimethylbenzene

1

2

34

5

6

C C

C C

C C

H CH3

CH3 H

H H

para-dimethylbenzeneor

1, 4 - dimethylbenzene

1

2

34

5

6

C C

C C

C C

H MD

MD H

H H

para-docsor

paradox

1

2

34

5

6

C C

C C

C C

H MD

H H

H MD

ortho-docsor

orthodox

1

2

34

5

6

C C

C C

C C

Fe2+ Fe2+

Fe2+ Fe2+

Fe2+ Fe2+

ferrous wheelor

ferris wheel

1

2

34

5

6

C C

C C

C C

H NO2

H H

H NO2

o - dinitrobenzeneor

1, 2 - dinitrobenzene

C C

C C

C C

CH3 NO2

H NO2

O2N H

2,4,6 - trinitrotolueneor

TNT

C C

C C

C C

Cl CH3

Cl H

H Cl

2, 4, 6 -trichloromethylbenzeneor

2, 4, 6 - trichlorotoluene

CH3

Toluene

C C

C C

C C

H O

H H

H COOH

2-acetyloxybenzoic acidor

(acetylsalicylic acid or aspirin)

C CH3

O

C

dichlorodiphenyltrichloroethaneor

DDT

C C

C C

C C

H H

H H

Cl C

C C

C C

C C

H H

H H

Cl

H

CCl3Cl

ClCl

C C

C C

C C

H CH

H H

H H

phenyl etheneor

styrene

CH2

n

poly aka (styrofoam)

Carboxylic Acids

COOH

NO2

COOH

Benzoic acid

p-Nitrobenzoic acid

CH3CHCH2CH2COOHBr

4-Bromopentanoic acid

CH2CH2COOHCl

3-Chloropropanoic acid

R – C – OH

=

O

R - COOH

Classes of Organic CompoundsClass of

Compoundhalocarbon

alcohol

ether

aldehyde

ketone

carboxylic acid

ester

amine

amide

FunctionalGroup

GeneralFormula Example

CH3ClchloromethaneCH3CH2CH2OH

1-propanolOH

O

C

O

C

O

C

O

OH

C

O

O

C

O

NH2

NH2

F, Cl, Br,I

OH

O

C

O

X

C

O

C

O

OH

C

O

O

NH2

C

O

NH2R

R

R R’

R

R R’

R

R R’

R

R

CH3CH2CH2NH2

propanamine

CH3CCH3

propanone

O

CH3CH2CHpropanal

O

CH3CH2COHpropanoic acid

O

CH3COCH3

methylethanoate

O

CH3CH2CNH2

propanamide

O

CH3OCH2CH3

methoxyethane

H

Organic Nomenclature Flow Chart

Functional Groups

Functional Groups

Timberlake, Chemistry 7th Edition, page 403

Order of Priority of Functional Groups

1 Carboxylic acid -COOH

2 Sulfonic acid -SO3H

3 Ester -COOR

4 Acid chloride -COCl

5 Amide -CONH2

6 Nitrile -CN

7 Aldehyde -CHO

8 Ketone -CO

9 Alcohol -OH

10 Phenol -OH

11 Thiol -SH

12 Amine -NH2

13 Ether -OR

14 Sulfide -SR

Order ofpriority Functional group Formula

Order ofpriority Functional group Formula

Selinger, Chemistry in the Marketplace, 1994, page 23

Esters

An ester is similar to a carboxylic acid, but the acidic hydrogen has been replaced by an alkyl group

H

OC C C

H

H

OHH

H

a carboxylic acid

H

OC C C

H

CH3

OHH

H

an ester

methyl propanoate

methyl group

propanoic acid

from propanoic acid

R – C – O – R’

O

Naming Esters

Name the following ester: CH3CH2CH2COCH2CH3

O

Step 1) the ester alkyl group (R’) = ethyl

Step 2) the acid (R) = butanoic acid

Step 3) the name = ethyl butanoate

R – C – O – R’

O

Formation of an Ester

H

OHC C C

H

OHH

H

C

H

H +

H

C H

H

H

C

H

HO

H

OC C C

H

OHH

H

C

H

H

+

H

C H

H

H

C

H

HOH

butyric acid (butanoic acid) ethyl alcohol

ethyl butyrate (tastes and smells like pineapple)

D

water

Ester Lab II

Ester Lab I

H

C C H

H

HH

H CC C

H H

HOH

2-pentanone

C5H10O

Ketone

R'R C

O

1 2 3 4 5

methyl propanoate

C4H8O2

Ester

H

C H

H

C OC C

H

OH

H

H

H OR C

O

R'

R'

123

3 carbons = propane

1) Name the R' first2) Find carbon chain and include the carbonyl carbon.3) Drop the ending and add -yl

(R' = methyl)

Ester

H

C CH3

CH3

OH C

O

OR C

O

R'Raspberry

CH2 CH2H OC C

H

OH

C

Banana

CH2 (CH2)6H OC C

H

OH

CH3

Orange

CH3

CH3

CH3

PP Ester

Lab

Ester

OR C

O

R'CH2 CH2H OC C

H

OH

CH3

Pear

Peach

CH2H OC C

H

OH C C

C C

C C

H H

H H

H

CC

H

C

H

H

COH

O

H

C

H

H

C HH

H

H

3-methylpentanoic acid

COH

OR

Carboxylic acid

C6H12O2

COH

O

COH

O

12345

H

HCC C C

H H HH

HHHH

H OC C

H H

HH

R'OR

Ether

ethyl butyl ether (common name)or

ethoxybutane (IUPAC) C6H14O

H

CC C

H

H

HH

H CC C

H H

HH

OH

C HH

C HH

H

H

H

C8H18O

3-ethyl-3-hexanol

OHR

Alcohol

COH

OC

H

H

H

ethanoic acid

COH

OR

Carboxylic acid

C2H4O2

H

C C OH

H

HH

CHO

H

H

1,3-propanediol

OHR

Alcohol

C3H8O2

Draw structural formulas for the following:

a. 3-heptene

b. trichloromethane

c. 2-chloro-3-phenylhexane

d. 1,3-cyclopentadiene

e. toluene (methylbenzene)

f. 1,4-dibromobenzene

g. 2-bromo-3-methyl-2-butene

Write the condensed formulas for the following haloalkanes:

a. ethyl chloride (common name) or chloroethane (IUPAC)

b. bromomethane

c. 1-bromo-3-chlorocyclopentane

d. 1,1-dichlorocyclohexane

e. 2,2,3-trichlorobutane

f. 2,4-dibromo-2,4-dichloropentane

Write a correct IUPAC (or common name) for the following:

a. bromoethane (ethyl bromide)

b. 2,3-dichlorobutane

c. chlorocyclopentane

d. 2-bromo-4-chlorohexane

e. 1-chloro-1-fluorocyclobutane

Cl

Cl

F

CH3CH2Br

CH3CHCHCH3

Cl Cl

CH3CH2CHCH2CHCH3

Cl Br

Draw structures for the following:

1,1,1-trifluoroethanecis-2-butene1-heptyne2-chloro-4,5-diethylnonanecyclohexaneethylcyclopropanemeta-dichlorobenzene2,4,6-trinitrotolueneortho-iodotolueneethyl pentanoate2-bromohexanal

methyl propanamidepropoxypropane (propylpentyl ether)m-iodophenol1,3-propanedioic acidpropylamine1,4-butandiol3-chloropentanoic acid1,3-dibromo-2-propanonemethyl-3-chloropropyl ether3-hydroxy-1-pentyne

F

C C H

H

HF

F

1,1,1-trifluoroethane

C2H3F3

cis-2-butene

CH3

C CH H

H3C

C4H8

trans-2-butene

CH3

C CH

HH3C

HCC C C

H H HH

HHHH

CC CH H

HH

H

1-heptyne

C7H12

HCC C C

H H HH

HHHH

H CC C

H H H

HHHCH

HH

CH

HC

H

CH

H

HCC C

HHH

CH

H

H CC C

Br

H H

Cl

Cl

Chirality: Chiral vs. Achiral

Chiral Achiral

right shoe left mitt right-handed glass plate scissors

tennisracket

H

Br

I

Cl

Chirality

Timberlake, Chemistry 7th Edition, page 484

H

Cl

I

Br

H

Br

I

Cl

mirrorH

Cl

I

Br

“cis” and “trans” isomers

cis-2-butene trans-2-butene

Timberlake, Chemistry 7th Edition, page 414

C = CCH3H3C

HH

C = CCH3

H3C H

H

Geometric Isomers

(same side) (opposite side)

Isomerism

Geometric Isomers

trans cis

Stereoisomers(Structural Isomers)

mirror images

Other Functional Groups to Recognize

Ethers Amines Amides (“EETH erz”) (“uh MEENZ”) (“uh MIDZ” or “AM idz”)

–O– –N –C–N

=O

“coca-ine”“caffe-ine”“Tatoo-ine”

Organic Reactionscombustion of hydrocarbons OR compounds w/only

C, H, and O: products are…CO2 and H2OWrite the equation for the complete

combustion of 2-methyl-2-pentene.

Write the equation for the completecombustion of ethylbutanoate.

C6H12 + O2 CO2 + H2O6 69

O

O

C6H12O2 + O2 CO2 + H2O6 68

substitution: an H atom is removed and “something else” is put in its place-- In halogenation, a _______ atom replaces an H. halogen

Write an equation for the reaction

between ethane and chlorine.

+ Cl2 –C–C–HHH

HHH

–C–C–ClHH

HHH

+ HCl

If more chlorine is provided, the reaction will produce...

AND SO ON. –C–C–Cl

HHH

HH+ Cl2 –C–C–Cl

HHCl

HH+ HCl

Substitution occurs with aromatic compounds, too.

+ Br2

catalyst

+ CH3CH2Clcatalyst

Br

+ HBr

+ HCl

Ethylbenzene is an importantintermediate in the production

of styrene which, in turn, isused to make polystyrene.Roughly 25 million tons of

ethylbenzene are produced and used every year.

addition: a multiple bond is broken and two “things” are inserted

+ Br2

H C=C

H

H H–C–C–Br

HHBr

HH

+ HBrH

C=CH

H H–C–C–Br

HHH

HH

+ H2OH

C=CH

H H–C–C–OH

HHH

HH

H2SO4

H–C–C–C–C–HH

H

H

H+ Cl2 –C–C=C–C–

Cl HHH H

Cl HH

A specific addition rxn is hydrogenation, in which__ is added across a multiple C-C bond.H

-- requires a catalyst (usually a finely-divided _____) to rupture the multiple bond metal

–C–C–HHH

HHH

+ H2

H C=C

H

H H

catalyst

Another addition reaction is polymerization.

“lots” of ethylene

H C=C

H

H H H C=C

H

H HH C=C

H

H H polyethylene

–C–C–C–C–HH

HH

HH

HH

condensation(or elimination,or dehydration): _____ is a productwater

-- One reactant provides an __, the other provides an ___.

HOH

CH3CH2OH + CH3OH CH3CH2OH + CH3OH

NO2

+ H2O+ HNO3

H2SO4

CH3CH2–O–CH3 + H2O

wateralcohol m’c alcohol m’c an ether

Complex proteinmolecules are

made fromcondensation

reactions ofamino acids.

-- Amides can be formed in condensation rxns between carboxylic acids and amines.

Write the equation for the reaction betweenbutanoic acid and nitrogen trihydride.

O

OH

+ NH3

O

NH2

+ H2O

carboxylic acid amine amide water

Ammonia is the simplest amine.

Esterification is a condensation reaction between acarboxylic acid and an alcohol.

Write the equation for the reaction betweenbutanoic acid and 1-butanol.

O

OH HO

+

O

O

+ H2O

butanoatebutyl(the active substance in

the characteristicflavor/odor of pineapple)

Write the equation for the reaction between3-phenyl-2-propenoic acid and ethanol.

O

OH HO +

H2O +

-3-phenyl-2-propenoate

(the active substance inthe characteristic

flavor/odor of cinnamon)

ethyl

(i.e, ethyl cinnamate )

“When in doubt, make water.”

Mr. B

O

O

Amino Acid

Amine Ammonia Ammonium ion

NH21- NH3 NH4

1+

Polymers

polymermonomer homo

Jaffe, New World of Chemistry, 1955, page 603

chain

copolymer

monomer

Copyright © 2007 Pearson Benjamin Cummings. All rights reserved.

Polymerization

Polymers = Monomer + Monomer + …

Synthetic Polymers– Nylon– “plastics”– Vulcanized rubber– polyethylene

Natural Polymers– Silk– Proteins (amino acids)– Starch (sugars)

Polymers

Ethene (ethylene)

Chloroethene(vinyl chloride)

Polyethylene

Polyvinyl chloride (PVC)

Plastic bottles, film,insulation material

Plastic pipes andtubing, gardenhoses, garbage bags

H2C = CH2 – CH2 – CH2 – CH2 – CH2 –

H2C = CH

Cl

– CH2 – CH – CH2 – CH –

Cl Cl

Polymers

Teflon

Tetrafluoroethene

Ski and hikingclothing, carpets,artificial joints

Nonstick coatings

Propene (propylene)

CH3CH = CH2 – CH2 – CH – CH2 – CH – Polypropylene

CH3 CH3

F – C = C – F

FF– C – C – C – C –

FF FF

FF FF

Polymers

Polystyrene

Plastic filmand wrap

Plastic coffeecups and cartons,insulation

Phenylethene

H2C = CH – CH2 – CH – CH2 – CH –

1,1 Dichloroethene

H2C = C – Cl

Cl – CH2 – C – CH2 – C –

Saran

Cl Cl

Cl Cl

Slime

PVA + PVA + PVA

– With cross-linking agent(borax solution)

What are some things you think of when I say organic?

• Medicine• Plastics• Soil• Soap• Petroleum• Grass• Clothing

PRISM fellow: Mr. Kevin J. Hodel

• Organic - the study of carbon containing compounds that their properties

• Why carbon?? Strong bonds

between carbons Low reactivity of

carbon compounds Geometry of carbon

compounds

PRISM fellow: Mr. Kevin J. Hodel

Diamonds

PRISM fellow: Mr. Kevin J. Hodel

Graphite

PRISM fellow: Mr. Kevin J. Hodel

Polymers

• Polymer - a large organic molecule composed of smaller units bonded together

– These smaller units are called monomers.• Tires

– Vulcanized rubber was discovered by mistake!!

• soft and weak until heated then forms disulfide linkages between the rubber polymers.

PRISM fellow: Mr. Kevin J. Hodel

Natural Polymers

• Rubber• Cotton• Paper

– Cotton and paper are made of cellulose which is the most abundant natural polymer in the world.

• Starch– Potatoes, corn, bread

PRISM fellow: Mr. Kevin J. Hodel

Synthetic Polymers

• Half of the industrial chemists work in some area of polymer chemistry.

• In 1996, more than 270 lbs of plastic was produced per person in the US.

PRISM fellow: Mr. Kevin J. Hodel

Types of Synthetic Polymers• Elastomers - can be highly stretched

and returns to their original shape.

• Fibers - polymers that exhibit little or no elasticity (threadlike)

• Plastics - synthetic polymers that are more elastic than fibers but less elastic the elastomers.

PRISM fellow: Mr. Kevin J. Hodel

Common Polymers• Polystyrene foam can be made into cartons to protect eggs or into

packing “peanuts” to cushion fragile objects for shipping.

• Polyethylene: You probably see polyethylene every day! It’s the plastic used to make many containers, among other things.

• Water-resistant paints and varnishes derive from a family of synthetic polymers called acrylics.

PRISM fellow: Mr. Kevin J. Hodel

Polystyrene

Plastic coffeecups and cartons,insulation– CH2 – CH – CH2 – CH –

PolyethylenePlastic bottles, film,insulation material

– CH2 – CH2 – CH2 – CH2 –

Recycling• Before: Milk jug.

After: Picnic table.

• Before: Bread bag. After: Trash can.

• Before: Sandwich box.

After: Frisbee.

PRISM fellow: Mr. Kevin J. Hodel

Plastic Resin Codes

Copyright © 2007 Pearson Benjamin Cummings. All rights reserved.

Addition Reactions

H

C C

H

H

HH

H

Br

C C

H

H

BrH

H

HC C

H

HH

HC C

H

HH

NiH – H +

NiBr – Br +

Acid-Catalyzed Hydration

H

C C

OH

H

HH

HH

C CH

HH H2SO4H – OH +

ethene ethanolwater

Write out the mechanism for the formation of isopropyl alcohol (used as rubbing alcohol), from propene.

OH

C C

H

H

HH

HH

C CH

HHH – OH

H2SO4

+

ethene ethanolwater

Molecular GeometryH

H

H

H109.5o

C

Linear Trigonal planar

Tetrahedral

Trigonal pyramidalBent

109.5o

107.3o104.5o

H2O CH4 AsCl3 AsF5 BeH2 BF3 CO2

180o

Order of Priority of Functional Groups

1 Carboxylic acid -COOH

2 Sulfonic acid -SO3H

3 Ester -COOR

4 Acid chloride -COCl

5 Amide -CONH2

6 Nitrile -CN

7 Aldehyde -CHO

8 Ketone -CO

9 Alcohol -OH

10 Phenol -OH

11 Thiol -SH

12 Amine -NH2

13 Ether -OR

14 Sulfide -SR

Order ofpriority Functional group Formula

Order ofpriority Functional group Formula

Selinger, Chemistry in the Marketplace, 1994, page 23