Organic

Kinds of Hydrocarbons

• Aliphatic– Chains or rings of carbon atoms– May be planar or non - planar

• Aromatic– Planar molecules– Usually contain one or more benzene rings

Aliphatic Hydrocarbons

• Hydrocarbons - contain only C and H

• Names of carbon chains # of C atoms Root Name

1 meth - 2 eth - 3 prop - 4 but - 5 pent - 6 hex - 7 hept - 8 oct - 9 non - 10 dec -

Alkanes

• Saturated hydrocarbons• Contain no double or triple bonds• Naming

– Root name + ane

• General Formula: CnH2n+2

H H H

H C C C H

H H H

CH3CH2CH3

propane

Alkenes

• Unsaturated hydrocarbons• Contain one double bond• Naming

– Root name + ene

H H H

H C C C H

H

CH3CHCH2

propene

• General Formula: CnH2n

Alkynes• Unsaturated hydrocarbons• Contain one triple bond• Naming

– Root name + yne

• General Formula: CnH2n-2

H

H C C C H

H

CH3CCH

propyne

Cycloalkanes

• Unsaturated hydrocarbons

• Contain one ring

• Naming– Cyclo + root name+ ane

H H

H H

H H H H

H H

H H

cyclohexane

C6H12

General formula: CnH2n

Alkdienes

• Unsaturated hydrocarbons

• Contain 2 double bonds

• Naming: root name + diene

H H H

C C C C

H H H

CH2CHCHCH2

butadiene

General Formula: CnH2n-2

Positional Isomers

Positional Isomers occur when the hydrocarbon can have a multiple bond (or functional group) in a different location.

Butene(C4H8)

4 carbon chain

1 double bond

H H H

C C C C H

H H H H

H H

H C C C C H

H H H H

1-butene

2-butene

Functional Groups

Oxygen Containing

Alcohol R - O - H

Naming Root name + bonding + ol

CH3CH2CH2OH propanol

CH2CHCH2OH propenol

Ether R - O - R

Naming R and R :Root name with yl ending + ether

CH3CH2OCH3 Ethyl methyl ether

Aldehyde R - CHO

Naming Root name + bonding + al

CH3CH2CHO propanal

CH2CHCHO propenal

Ketone

O

R - C - R

Naming Root Name + bonding + one

CH3CH2COCH3 butanone

CH2CHCOCH3 butenone

Carboxylic Acid O

R - C - O H

Acidic H

Naming Root name + bonding + oic acid

CH3CH2CH2COOH Butanoic acid

Lose acidic H, yields anion

CH3CH2CH2COO - Butanoate ion

Ester O

R - C - O R’

Naming R ’ alkyl + root name + bonding + oate

O

CHe CH2 CH2 C O CH2 CH3

ethyl butanoate

Anhydride O O

R C O C R

Two acids joined together with the loss of water

Naming

We will limit to both acids the same

Acid name + anhydride

O O

CH3CH2CH2 C O C CH2CH2CH3

Butanoic anhydride

Nitrogen containing functional groups

Amines

Primary amine (1o) R - NH2

Secondary amine (2o) R,R ‘NH

2 H on N

1 H on N

Tertiary amine (3o) R,R ‘R”N 0 H on N

Naming R, R’ , R” named as alkyls + amine

CH3NH2 methylamine

(CH3)(CH3CH2)NH ethylmethylamine

(CH3)3N trimethylamine

Amide RCONH2

OR- C-NH2

Naming Root + bonding + amide

O

CH3CH2C - NH2

propanamide

Can substitute on the N, name as alkyl prefix

O

CH3CH2C - NHCH3

Methylpropanamide

Common Substituents

- Cl chloro

- Br bromo- I iodo

- NO2 nitro- NH2 amino

- OH hydroxy

- R alkyl (hydrocarbon added to primary chain)

Common names of some organic substituents

CH3

CH

CH3

isopropyli - propyl

CH3

CH CH2

CH3

isobutyli - butyl

CH3

H3C C

CH3

tertiary butylt - butyl

CH2 CH vinyl

Naming substituted hydrocarbons

1. Name the longest chain

2. Add the compound type (suffix)

3. Add prefix to indicate any substituents or branches

4. Indicate the position with a number for the carbon it is attached to.

O

CH3 CH CH2 CH2 CH

CH2 CH3

hexanal4-methyl

What is the BEST name for :

O

CH3 CH CH2 C CH3

ClA)ChloropentanoneB)2-chloro-4-pentanoneC)4-chloro-2-pentanoneD)2-chloropentanalE)4-chloro-1-methylbutanone

What is the BEST name for :

O

CH3 CH CH2 C CH3

ClA)ChloropentanoneB)2-chloro-4-pentanoneC)4-chloro-2-pentanoneD)2-chloropentanalE)4-chloro-1-methylbutanone

What is the BEST name for:

(CH3CH2)2NH

A)Ethyl amideB)DimethylamineC)1,1-ethylamineD)DiethylamineE)diethylamide

Common Names

carbontetrachloride CCl4chlorform CHCl3Methylene chloride CH2Cl2methylchloride CH3Cl

freon CCl2F2

acetone O

CH3 - C - CH3

acetic acidO

CH3 - C - O - H

O

CH3 - C - O

Acetate ion

acetaldehyde O

CH3 - C - H

formaldehyde O

H - C - H

Formic acid O

H - C - O - H

(di)ethylether CH3CH2OCH2CH3

CH3CH2OH Ethyl alcohol

CH3OH Methyl alcohol

Oxalic acidO O

H - O -C - C - O - H

GlycerineO - H O - H O - H

CH2 - CH - CH2

glycerol

1,2,3 - propanetriol

NO2 NO2 NO2

O O O

CH2 - CH - CH2

nitroglycerine

urea O

H2N C NH2

Aromatic Compounds

All contain benzene rings (C6H6) H H

H H

H H

H H

H H

H HResonanceforms

Electrons shift so quickly that they are called delocalized electrons.

Add extra stability

Benzene is represented by

Naming monosubstituents

CH2CH3

ethylbenzene

R

alkylbenzene

Cl

chlorobenzene

NH2

aminobenzeneaniline

NO2

nitrobenzene

More than 1 substituent need to identify where

1

2 3

4

56

2 the sameBr Br

1,2 - dibromobenzene

ortho - dibromobenzene

o - dibromobenzene

Br

Br

1,3 - dibromobenzene

meta - dibromobenzene

m - dibromobenzene

Br

Br

1,4 - dibromobenzene

para - dibromobenzene

p - dibromobenzene

Br

NO2

1,3 - bromonitrobenzene

meta - bromonitrobenzene

m - bromonitrobenzene

If benzene is used as an attachmentIt is called phenyl

CH3

CHCH3

2 - phenylpropane

Fused benzene rings - share 2 C’s

Polycyclic compounds

naphthalene anthracene

/115 letter56.35 D60.95 D+65.55 C-71.3 C77.05 C+82.8 B-88.55 B94.3 B+

100.05 A-105.8 A

Average = 85.7Median = 89

Exam 1

Frequency

0

5

10

15

20

25

30

35

0 6

12

18

24

30

36

42

48

54

60

66

72

78

84

90

96

102

108

114

120

126

Frequency

More Common NamesContain Benzene

O

C - OH

O

O - C - CH3

AspirinAcetasalicyclic acid

OH

phenol

O

C - OH

Benzoic acid

biphenyl

naphthalene anthraceneCl

p - dichlorobenzene

NH2

anilinephenylamineaminobenzene

Cl

CH3

toluene

CH3

2,4,6 - trinitrotolueneNO2

NO2

O2N

TNT

Dicarboxylic Acids

Oxalic Acid

O O

H O C C O H

Malonic Acid

O O

H O C CH2 C O H

Succinic Acid

O O

H O C CH2 CH2 C O H

Dicarboxylic Acids

Glutaric Acid

O O

H O C CH2 CH2 CH2 C O H

Adipic Acid

O O

H O C CH2 CH2 CH2 CH2 C O H

Oh My Such Good Apples