Chlorination of Acetylene

- Study of carbon and carbon compounds

- Carbon forms covalent bonds ( e neg diff < 1.7) with many other atoms

- Huge chains of C to C bonds, rings, networks

-petroleum, coal, wood, animals, other plant products

Characteristics of Organic Compounds Characteristics of Organic Compounds ( covalent ( covalent substances )substances )

1. Low M.P. and B.P. (have weak intermolecular forces)

2. Nonconductors ( e- are not free to move around)

3. Nonpolar therefore won’t dissolve in polar substances like water - only dissolve in other nonpolars

- - Like Dissolves LikeLike Dissolves Like

4. React Slowly ( bonds between atoms are relatively strong )

- Are nonelectrolytes

- Exception organic acids (CH3COOH)

- Usually exist as gases, liquids or low m.p. solids

Types of BondsTypes of Bonds

1. Carbon has 4 valence electrons : can form 4 covlent bonds

CC2. Two carbons can form a covalent bond; single bond- One pair of shared electrons

- If all bonds between carbons are single the molecule is called saturatedsaturated

CC CC

3. If two pairs of electrons are shared between carbon atoms, double bond results

-organic compounds with double or triple bonds are said to be unsaturatedunsaturated

CC CC4. If three pairs of electrons are shared a triple bond is formed

CC CC

Molecular Formula- Shows number and type of elements in a compound

Ex. CH4

Structural Formula -shows elements and the arrangement of atoms

HH C H H

- Each line represents a pair of shared electrons

Isomers - Compounds with the same molecular molecular formulaformula but different structural formulastructural formula

- All have molecular formula C6H14

- Have different properties

HydrocarbonsHydrocarbons

- Contain only C and H

- Names are based upon longest carbon chain

- Organized into homologous series

- As molecular size increases the b.p. and f.p increase due to stronger intermolecular forces

- Members increase by one C and some H’s

Alkanes Alkanes Table QTable Q

- A homologous series of saturatedsaturated hydrocarbons

C C CCC

-all single covalent bonds

- Have the general formula CnH2n + 2 Table QTable Q

- Named according to the IUPAC system of nomenclature

- Prefix – denotes number of carbon atoms

Meth 1 carbon atom

Eth 2 carbon atoms

Prop 3 carbon atoms

but 4 carbon atoms

pent

5 carbons

Table P has all the prefixes you’ll need to Table P has all the prefixes you’ll need to know!!!know!!!

Alkanes always end in name –ane Table QTable Q

H - - H

H |

H |

H |

H |

H |

H |

H |

H |

H |

H |

H - - H

H |

H |

H |

H |

H |

H |

H |

H |

H - - H

H |

H |

H |

H |

H |

H |

H - - H

H |

H |

H |

H |

2. Naming alkanes

# of prefix alkane Structural formula molecular formula carbons

1.

2.

3.

4.

5.

meth methane

but

prop

eth

pent

ethane

propane

butane

pentane

CH4

C2H6

C4H10

C3H8

C5H12

HH C H H

C-- C

C--C --C

C--C --C --C

C--C --C -- C-- C

All end in “ane”. The prefix indicates the number of carbons in the longest chain

- Butane is the first alkane that can exist as an isomer

-As the number of C in the molecule increases the number of isomers also increases

Isomers of pentane

Alkyl Groups - An alkane with one less H CnH2n + 1

- Are side groups on longer chains

- End in - yl

CH3 – methyl group

C2H5 – ethyl group

IUPAC System for Naming Alkanes

1. Use ane ending

2. Attach prefix to show number of carbon atoms in longest chain

| | | |- C - C - C - C - | | | | |

- C - |

| - C - |

A.hexane | | | |

- C - C - C - C - | | | |

| - C - |

| - C - |

| - C - |

B.

hexane | | | |- C - C - C - C - | | | |

| - C - | |

- C - |

| - C - | |

- C - | | - C - |

C.

heptane

3. If there are side branches, number the parent chain from which end reaches the branch soonest H

|H- CHH H H | | | |H - C - C - C - C - H | | | | H H HCH H | H

4. Determine name for each branch5. Write the complete name for the compound. Place a number in front of side chain to indicate where it occurs on parent chain.

H H H H H H | | | | | |H - C - C - C - C - C - C - H | | | | | | H HHCH H H H | H - C - H | H

2-methyl pentane

3-ethyl hexane

6. If there are two or more identical alkyl groups use prefixes: di (2); tri (3) ; tetra (4). Use numbers seperated by commas to identify the location of the groups.

CH3 CH CH CH3

CH3

CH3

2,3 – dimethylbutane

Practice - Name the following hydrocarbons

H |H- CHH H H H H | | | | | |H - C - C - C - C - C- C -H | | | | | | H HHCHH H H | H

H | HHCH H H H H | | | | | |H - C - C - C - C - C - C - H | | | | | | H HHCH H H H | H

H | H H HCH H H H | | | | | |H - C - C - C - C - C - C - H | | | | | | H H HCH H H H | H-C-H | H

H H H H H H H H | | | | | | | |H - C - C - C - C - C - C - C - C - H | | | | | | | | H H HHCH H H HCH H | | HCH H | HCH | H

a. b.

c.d.

heptane

hexane octane

hexane4-methyl 2,3- dimethyl

3-ethyl 3-methyl 2-methyl 5-propyl

Practice - Name the following compounds.

A.

B.

C.

CH3

| CH2 - CH2 - CH - CH2 - CH3

| CH3

CH3

|CH3 - CH2 - C - CH2 - CH3

| CH3

CH3 – CH2 - CH2 - CH - CH2 - CH2 - CH3

| CH2

| CH2

| CH3

3- methyl hexane

3,3- dimethyl pentane

4-propyl heptane

AlkenesAlkenes- A homologous series of unsaturatedunsaturated hydrocarbons containing ONE double bond CnH2n- To name change end of alkane to eneene

- Hydrocarbons with more than 1 double bond are not alkenes

Name Formula Structure

Ethene C2H4

                          

Propene C3H6

                                         

Butene C4H8

                                                 

AlkynesAlkynes - Homologous series of unsaturated hydrocarbons containing ONE triple bond CnH2n-2

- To name change ane ending to -yneyne

Other Organic CompoundsOther Organic Compounds

- Occur when one or more H’s are replaced by other elements- Are usually named from corresponding hydrocarbon

Functional Group -Functional Group -A particular arrangement of a few atoms, giving characteristic properties to an organic molecule

Ex. - OH alcohols- COOH organic acids

- CHO aldehydes

Halides - Normal alkanes with group 17 element substituted in for a H

H Br | |H - C - C - H | | H H

1-bromoethane

Naming substituted alkanesNaming substituted alkanes

a. The longest chain of carbon atoms is the base name

Cl H | |H - C - C - H H H H

| | | | | H H-C - C - C - C - H

| | | | H H H H

This has six carbons in the longest chain, so it is some form of

Hexane

b. Write the halogen group name before the base name

Cl Br F IChloro Bromo Fluoro Iodo

c. Name the location of the extra group

Since the chlorine is on the first carbon, it is

1-chloro

HexaneChloro1-

Important pointImportant pointImportant pointImportant point

The hydrocarbon chain is numbered so that the extra groups have the lowest number possible

Start numbering the chain on the side closest to the extra group

H H

| |H - C - C - H H H H

| | | | | H H-C - C - C - C - H

| | | | H H Cl H

124

56This is 2-chloro hexane, not 5-chloro hexane

3

Name these compounds

They are actually the same, one is just flipped over.

H H | |H - C - C - Br | | H H

H H | |Br- C - C - H | | H H

2-bromo ethane1-bromo ethane

H H | |H - C - C - Br | | H H

H H

| |

H - C

- C - Br

| |

H H

H H

| |

H - C

- C - B

r

| |

H H

H H

| |H

- C - C

- Br

| | H

H H H

| |

H - C - C - Br

| |

H H H H | |Br- C - C - H | | H H

To avoid this

Examples - Name the following

H Cl H H

| | | | H-C - C - C - C - H

| | | | H H H H

H H

| |H - C - C - H H H

| | | | H H-C - C - C - H | | | Br H H

I H | |H - C - C - H | | H H

a. b. c.

butanechloro2- pentanebromo3-

ethaneiodo1-

d. If a group appears more than once, we number both places and add di tri tetra to the halogen prefix

2 3 4 H H

| |H - C - C - H Cl H H

| | | | | H H-C - C - C - C - H

| | | | H H Cl H

This hexane has a chlorine on carbons #2 and #3

Called 2,3 - dichloro hexane

Examples - Name the following Cl Cl H H

| | | | H-C - C - C - C - H

| | | | H H H H

H H

| |H - C - C- H Br H

| | | | H H-C - C - C - H | | | Br Br H

I H | |H - C - C - H | | H I

a. b. c.

butanedichloro1,2-pentanetribromo2,2,3-

ethanediiodo1,2-

e. When different halogens are added, alphabetize the prefix names

Cl Br | |H - C - C - H H H H

| | | | | H H-C - C - C - C - H

| | | | H H H H

This has a Chlorine on #1 and a Bromine on #2, so bromine comes first

hexane2-bromo, 1-chloro

Examples - Name the following Cl F H H

| | | | H-C - C - C - C - H

| | | | H H H H

H H

| |I - C - C- H Br H

| | | | Cl H-C - C - C - H | | | Br Br H

I H | |H - C - C - H | | Cl I

a. b. c.

butane2-fluoro1 chloro

pentane1-chloro3,4,4-tribromo

ethane1,2-diiodo1-chloro

1-iodo

AlcoholAlcohols s

- One or more H’s have been replaced with OH group- Only one OH per carbon

-Alcohols are NOT bases OH does not form hydroxide ions in solution

-Are classified by:

1.) Number of –OH groups in molecule2.) Number of C chains attached to C that has the –OH on it

- When writing molecular formulas, the OH is written last

C2 H5 OHThe OH on the end indicates that it is an alcohol

H H | |H-C--C--OH | | H H

H O | |-C--C--OH | |

Example - Write out the molecular formula of the alcohols H |H-C--OH | H

H O H H | | |H-C--C--C--H | | | H H H

H | HCH H H | | |H-C--C--C--OH | | | H H HCH3

H9

H7 C4

C3

OHOH

OHNaming Alcohols

Replace the “e” of the alkane name with“ol”

We will only be looking at alcohols with single bondsWe will only be looking at alcohols with single bonds

H |H-C--OH | H

Name Common name

methane

Methyl alcohol Wood alcoholVery poisonousused as a laquer thinner

ol

H H | |H-C--C--OH | | H H

ethanol Ethyl alcohol Mild poison (large doses kill)Used in liquor, medicine

Monohydroxy alcohols - Have only one OH group

Primary alcohols – the OH is attached to an end carbon

H H H | | |H-C--C--C--OH | | | H H H

H H | |H-C--C--OH | | H H

No special naming rules

propanol ethanol

Secondary Alcohol -OH is in the middle of a chainCarbon holding the OH has two other carbons attached to it

H H O H H | | | |H-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 H O H H

Must number the carbon chain and name the location of the OH

butanol2- hexanol2-

Examples - Name the following alcohols

Br H H H H | | | | |H-C--C--C--C--C--H | | | | | H H H O H H

H | H H HCH H

| | | |H--C--C--C--C--OH | | | | H H H H

Butanol2-methylPentanol2-5-bromo

The carbon chain is numbered for the functional group

Dihydroxy alcohols

Have two hydroxyl groups

Named by adding “diol” to the alkane name. (keep the “e”)Must name the location of both alcohol groups

H H | |H-C--C--H | | O O H H

ethanediol1,2-Commonly called ethylene glycolCommon component of antifreeze

Written as C2H4(OH)2

EXTRA

Trihydroxy alcohols

Have three OH groups attachedAdd “triol” instead of “diol”

H |H-C-OH |H-C-OH |H-C-OH | H

called1,2,3-propanetriolCommonly calledGlycerine or GlycerolUsed in fat production

Practice - Name the following alcohols H |H-C-OH |H-C-H |H-C-OH | H

H |H-C-Br |H-C-OH |H-C-OH | H

Br H H H H | | | | |H-C--C--C--C--C--H | | | | | H O O H O H H H

1,3-propanediol

3-bromo 1,2 propanediol

5-bromo 1,3,4-pentanetriol

Written as C3H5(OH)3

Organic AcidsOrganic Acids-the functional group is the carboxyl group

O ||--C--OH

In solution, it is the H from the OH that is creates the H+

Always written as “COOH” at the end of the molecular formula

H H H O | | l ||H-C--C--C--C--OH | | | H H H

C3H7COOHThis is how you recognize an organic acid

R - COOH

Practice - Write out the molecular formula for the following

H H O | | ||H-C--C--C--OH | | H H

O ||H--C--OH

O H || |HO-C--C--H | H

C2H5COOH HCOOH CH3COOH

Naming Organic Acids

Take the longest alkane chain, remove the “e” and add “oic acid”

O ||H--C--OH

Methanoic acid Commonly called Formic acid

H O l ||H-C--C--OH | H

Ethanoic acid Commonly called Acetic acid

Example - Name the following acids

H H O | | ||H-C--C--C--OH | | H H

H H O | | ||H-C--C--C--OH | | HCHH | H

O H H H H || | | | |HO-C--C--C--C--C--H | | | | H H Cl H

Propanoic acid Butanoic acid Pentanoic acid4,4-dichloro

Aldehydes

Functional group O ||-C-H

Naming- remove the “e” from the alkane and adding “al”

Solvents, embalming

R-CHO

Structural Formula

Name

Common Name

Uses

Molecular formula

O ||H--C--H

H O | ||H--C--C--H | H

O H H || | |H--C--C--C--H | | H F

methanal

formaldehyde

Preserving fluidirritating to lungs

CH2O

ethanal

acetaldehyde

Used to makesynthetic rubber

C2H4O

3-fluoro propanal

C3H4OF

Ketones

Functional group

Must have at least one carbon on either side

Naming - remove the “e” from the alkane and adding “one”

O ||--C--

Double bonded oxygen is in the middle of a chain

Solvents manufacturing of plastics

Structural Formula

Name

Common Name

Uses

Molecular formula

H O H | || |H--C--C--C--H | | H H

H H O H | | || |H--C--C--C--C--H | | | H H H

H O H H H | || | | |H--C--C--C--C--C--H | | | | H H Cl H

propanone

Acetone

Nail polish remover

CH3COCH3

2-butanone

CH3COC2H5 CH3COC3H6Cl

4-chloro 2-pentanone

Functional group

Must have at least one carbon on either side

Naming - alphabetize the two groups on either side of the --O--, then add the word “ether”

Molecular formula - Starting with the shorter side,write everything before the --O--, then write “O”, then write everything after

Ethers--O--

Anesthietics

Structural Formula

Name

Common Name

Uses

Molecular formula

H H | | H--C--O--C--H | | H H

H H H H H | | | | |H--C--C--C--O--C--C--H | | | | | H H H H H

Dimethyl ether

CH3OCH3 C2H5OC3H7

Ethyl propyl ether

Amine

Functional group

Naming- remove the “e” from the alkane and adding “amine”

Methanamine, propanamine

H |--N--H

Amino acids, manufacture of plastics, dyes H |--N--

Structural Formula

Name

Molecular formula

H H H | | |H--C--C--N--H | | H H

H H H H | | | |H--N--C--C--C--H | | | H H H

ethanamine

C2H5NH2

propanamine

C3H7NH2

Special compounds Amino Acids

Contains an amine group and an acid group attached to a carbon

H |H – N -

H |C |R

O ||- C – OH

amine Carboxyl (acid)

The “R” can be any atom or group of atoms.

Basic building blocks of all proteins in the body.

When amino acids combine, they form an AMIDE

H |H – N -

H |C |R

O ||- C – OH

H |H – N -

H |C |R

O ||- C – OH

H2O

H |H – N -

H |C |R

O ||- C –

H | N -

H |C |R

O ||- C – OH

Amide

Functional group

Naming - remove the “e” from the alkane and adding “amide”

O H || |- C--N--H

Proteins, medicines

Structural Formula

Name

Molecular formula

H O H | || |H--C--C--N--H | H

H O H H | || | |H--N--C--C--C--H | | H H

ethanamide

CH3CONH2

propanamide

C2H5CONH2

O H || |- C--N--

Generally,organic reactions occur slower than inorganic reactions

Many reactions require a catalyst to lower the activation energy

Substitution Reaction

Halogen gas + saturated hydrocarbon

One atom in the halogen gas switches places with one of the hydrogens in the hydrocarbon (halogenation)

Creates a substituted hydrocarbon and an acid

H H H | | |H--C--C--C--H | | | H H H

Br - Br

BrBr

HH

BrHBr

H

- Replace one kind of atom or group with another

If a second halogen gas is added, another substitution will occur

If we repeat this process 4 times with chlorine and methane, we get

If we take methane and do 2 chlorine substitutions and 2 fluorine substitutions, we get

Carbon tetrachloride

Dichloro difluoromethane

Freon

H H H | | |H--C--C--C--H | | | H H H

H Br H | | |H--C--C--C--H | | | H H H

H Br H | | |H--C--C--C--Cl | | | H H H

+ Br2-->

HBr

+ Cl2 -->

HCl

H |H--C--H | H

+ 4 Cl2

Cl |Cl--C--Cl | Cl

+ 4 HCl

H |H--C--H | H

+ 2 Cl2

+2 F2

Cl |F--C--F | Cl

+ 2 HCl and 2 HF

Addition ReactionHalogen + Unsaturated hydrocarbon

- When the double bond breaks, we have two open bonding sites

Both of the halogen atoms are added

H H | |H--C--C C--C--H | | | | H H H H

F--FFFFFF

FFF

F

We only have one product!We only have one product!

- Usually involves adding one or more atoms at a double or triple bond- Resulting molecule is saturated

Don’t Write whats next!!!

“Hydrogenation” H H H | | /H--C--C==C | \ H H

+ H2 -->

H H H | | |H--C--C--C--H | | | H H H

H H H | | |H--C--C==C--C--H | | | H H H

+ Br2

H H Br H | | | |H--C--C--C--C--H | | | | H Br H H

2,3-dibromobutane

Fermentation

- Glucose is broken down by enzymes to make alcohol and carbon dioxide

C6H12O6

zymase2 C2H5OH + 2 CO2

glucoseenzyme

ethanol

Notice how the OH from acid and H from alcohol are removed

This is a type of Dehydration Synthesis

Removal of water to create a bond

EstersEsters

Functional Group

In a molecular formula, written as

EsterificationOrganic acid + alcohol --> ester + water

H H O | | ||H--C--C--C--OH | | H H

H H H | | |HO--C--C--C--H | | | H H H

H H H | | | O--C--C--C--H | | | H H H

H H H | | |HO--C--C--C--H | | | H H H

H H H | | | O--C--C--C--H | | | H H H

H H H | | | O--C--C--C--H | | | H H H

H2O

O ||--C--O--

COO

This will appear in the middle of a formula

- Fruity odor

Named by taking the groups name of the alcohol, then by taking the “oic acid” and changing it to “oate”

Examples

H H O | | ||H--C--C--C-- | | H H

H H H | | | O--C--C--C--H | | | H H H

Acid side Alcohol side

C2H5 COOC3H7

H H O | | ||H--C--C--C-- | | H H

H H | | O--C--C--H | | H H

Ethanol

Ethyl

Propanoic acid

propanoate

H O | || H--C--C-- | H

H H H | | | O--C--C--C--H | | | H H H

Propyl ethanoate

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

SaponificatioSaponificationn - Hydrolysis of an ester in presence of a fat to make

soap

Combustion (oxidation)Combustion (oxidation)

- With excess oxygen; hydrocarbons burn completely to form carbon dioxide and water

CH4 + 2 O2 CO2 + 2 H2O

Polymerization

- The formation of a larger molecule from a smaller onePolymer - Chains of small units bonded together

Natural Polymers – starch, cellulose, proteins

Synthetic Polymers – nylon, polyethylene ( plastic)