Chem Module 3

Features of Organic Compounds

1. All organic compounds contain C

2. Carbon forms single, double, and triple bonds

3. Some carbons form chains and some form rings

4. Heteroatoms = atoms other than C and H

All organic compounds contain

Carbon

Carbon forms

single, double, and triple bonds

Heteroatoms

atoms other than C and H

ane

means all single bonds (ex. propane)

Methane

Common organic compound CH4

Ethane

C2H6

All bonds are single bonds

C - C

Double bonds

Contain four electrons

Ethylene

One double bond between carbons

C=C

Triple bonds

Contain six electrons

C≡C

Acetylene

One triple bond between carbons

Cyclo

ring

*Number of Bonds formed

H - one bond, 0 lone pairs

O - two bonds, 2 lone pairs

N - three bonds, 1 lone pair

C - four bonds, 0 lone pair

Halogen (group 7) one bond, 3 lone pairs

Linear

Atom surrounded by two groups, shaped like a line

Ex. Acetylene H-C≡C-H

Trigonal planar

Atom surrounded by three groups

(Bond angle- 120)

Ex. Ethylene

Tetrahedral

Four groups around an atom

*All Carbons with 4 single bonds are tetrahedral

Trigonal Pyramidal

Four groups surrounded and one group is a lone pair

Ex. Nitrogen surrounded by 3 atoms + 1 lone pair

Bent

Four groups surround, two groups are lone pairs

Ex. Oxygen surrounded by 2 atoms + 2 lone pairs

Complete structure

Ball and stick model

Condensed structure

CH3CH2CH2CH2CH2CH3

Skeletal structure

Alkanes

Single bond

C-C

Alkenes

Double bonds

C=C

Alkynes

Triple bonds

C≡C

Alcohol

Have a hydroxyl group (OH)

Organic Acid

Contain carboxyl Group

O

||

C — OH

R Functional Group

R bonded to a functional group

Ex: Alcohol R-OH

R

Called Alkyl group

Carbon backbone to which a functional group is bonded

Functional group

Atom or group of atoms having characteristic chemical and physical properties

Hydrocarbon

Type of Functional Group

Compounds that contain only hydrogen and carbon

Classified as Alkane, Alkene, Alkyne, and Aromatic compound

Alkane

All single bonds

C-C bond

ex. Methane CH4

Alkenes

At least one double bond

C=C

Ex. Ethylene C2H4 (gas that ripens bananas)

Alkyne

At least one triple bond

C≡C

Ex. Ethyne H-C≡—H aka acetylene

Aromatic compound

Based on benzene ring

Polyethylene

Made by Polymerizing ethylene where the double bonds in ethylene are broken to form single bonds joining adjacent ethylene molecules → polyethylene is an alkane

Compounds containing a single bond to a heteroatom

Type of functional group

Alkyl halides

R-X

R is an alkyl group

X is a halogen (Group 7A)

Alkyl group

Functional group composed only of carbon and hydrogen

Alcohol

R-OH

OH is hydroxyl group

Ethers

R-O-R

R and R are two alkyl groups

Amines

R-NH2 or R2NH or R3N

Thiols

R-SH

(where Garlic, onion, cheese, oysters, and skunk spray smell comes from)

Carbonyl group

C=O

Carbonyl compounds

Compounds containing C=O

Ex. Aldehydes, Ketones, Carboxylic Acids, Esters, Amides

Carboxylic acid

R—(C=O)—OH

Ketone

R—(C=O)—R

Aldehydes

R—(C=O)—H

Ester

R—(C=O)—OR

Amide

R—(C=O)—NH2

Hydrocarbons are nonpolar because

Only contrail C-C and C-H bonds

Nonpolar solute

Dissolves in nonpolar solvent

(Oils, lipids)

Hydrophobic

Polar solute

Dissolves in polar solute

(Water)

Hydrophilic

Fat soluble vitamins

A, D, E, K

Water soluble vitamins

B, C, H

Alkanes

Hydrocarbons having only C-C and C-H single bonds

ane- all single bonds

Meth

1 C

Eth

2 C

Prop

3 C

But

4 C

Pent

5 C

Hex

6 C

Hept

7 C

Oct

8 C

Non

9 C

Dec

10 C

Acyclic alkanes

Alkanes that have chains of carbon atoms but no rings

Alkanes with less than 4 carbon atoms

Gases at room temperature, used as heating fuels

Alkanes with 9 to 17 carbons

Liquids at room temperature, fuels

Alkanes with 25 or more carbons

Waxy solids

Octane

Volatile liquid at room temperature; gasoline

Alkanes with 18 or more atoms

Petroleum jelly

Unsaturated fatty acids

At least one C=C double bond

Saturated fatty acids

All single bonds between carbons

Oils

Liquid at room temp; low melting point

Low concentration of saturated fatty acids and high concentration of unsaturated fatty acids

Fats

Solids at room temperature, high melting point

High concentration of saturated fatty acids

Hydrogenation of Alkenes

Alkenes can be converted to alkanes by addition of hydrogens

Cis

Alkyl groups on same side of double bond and H atoms are on other side

Trans

Groups and H on opposite side of double bond