Chemistry 2202

Unit 3: Hydrocarbon Derivatives Name: _________________

Organic Compounds

Pure Hydrocarbons Hydrocarbon Derivatives

Alkyl Halides Aldehydes

Alcohols Ketones

Ethers Organic Acids

Amines Esters

Amides

Hydrocarbon Derivatives
- organic compounds containing C, H, and at least 1 other atom
- one of the H atoms is replaced by another atom to form a derivative
- includes alcohols, ethers, aldehydes, ketones, carboxylic (organic) acids, alkyl
(organic) halides, esters, amines, amides
- each hydrocarbon derivative has an alkyl stem and a functional group

Alkyl Stem - the continuous chain of C atoms on which a functional

group is attached to make it a HC derivative

Functional Group - an identifiable arrangement of atoms that gives a

compound certain chemical properties

1
Alkyl Halides
- a.k.a. halocarbons and organic halides
- Basic Formula R-X R - represents the parent HC chain
X - represents functional group

- Functional group - halogen atom such as F, Cl, Br, I

Properties
- few of these compounds found in nature
- mostly synthetic
- toxic, carcinogenic, flammable
- widely used as both anesthetics and insecticides
- involved in substitution reactions

Examples
- Chloroethane - (C2H5Cl) or (CH3CH2Cl) - local anesthetic - rapid cooling
of the skin deadens the nerve endings reducing pain
transmission to the brain.

- CFCs - chlorofluorocarbons
- used as refrigerant (freon)
- destroy ozone layer

- DDT - dichlorodiphenyltrichloroethane
- insecticide used between 1950s and 1970s (non-
biodegradable)
- leads to bioamplification in organisms

- PCB’s - polychlorinated biphenyls

- used as insulating fluid in electrical transformers and capacitors
- breaks down very slowly
- severe health effects
- strictly regulated in Canada (western world)

Naming Alkyl Halides

1. Indicate position of halogen atom on the longest continuous HC chain with the
halogen (number chain to give the atom lowest #).
2. Identify the halogen but change ending -ine to -o.
e.g. fluorine –> fluoro
If more than one halogen, use di, tri, tetra.
e.g. fluorine –> difluoro
3. Complete the name by naming C chain with appropriate prefix.
a. (Ex: 3 Carbons - propane)

2
Examples

Ex 1:

Name: 2,3,4-tribromo-3-ethyl hexane

Ex 2:

Name: 2,3-dibromo-2-methyl butane

Ex 3:

Name: 1,4-difluoro cyclohexane

Ex 4:

Name: 1,3-dibromo-4-methyl cyclohexane

Ex : 5

Name: 2,3,4-trichloro-2-bromo-3-
ethylpentane

3
Alcohols

Formula: R-OH where R - represents HC parent chain

OH - represents hydroxyl functional group
- OH not the same as hydroxide ion (OH-)
- based on ‘alkane’ parent chain

Properties
- liquids at room T
- flammable
- boil at higher T b/c of H-bonds
- polar (-OH) and non-polar (HC) ends
- short chains soluble in water

Examples

Methanol - CH3OH
- “wood alcohol” historically made by heating wood shavings in the
absence of air
- used as a fuel in some race cars
- toxic to humans if inhaled or drank
- drink 10 mL - blindness
-drink 30 mL - death

Ethanol - C2H5OH
- “grain alcohol” historically made by fermentation, where yeast cells
break down sugar to form ethanol
- solvent in drugs, food preparation, varnishes, perfume, flavouring
- intoxicating substance in “alcohol”
- depressant drug, liver damage, behaviour changes
- laboratory ethanol must be “denatured” (ex: methanol added)

Ethylene glycol
- C2H4(OH)2
- rubbing alcohol
- antifreeze -> -17.4oC
- add water -> -36oC
- kidney failure if ingested

4
 Naming Alcohols

1. Indicate location of -OH group (number HC chain to get lowest possible #).
2. Finish name as if naming an alkane, but change ending ‘e’ to ‘ol’.
e.g. 2 C chain - ethane -> ethanol
3 C chain with OH on C#2 = 2-propanol

Ex 1

Name: Methanol

Ex 2

Name: Ethanol
Ex 3

Name: 2-Propanol (rubbing alcohol)

Ex 4

Name: Propanol (wax solvent / paint

laquer)

Ex 5 OH

Name: 2-methyl-2-butanol
Ex 6

Name: 3-methyl-1-butanol

5
 Alcohol Type

Depending on the position of the hydroxyl (OH) group, the alcohol can be either
primary, secondary or tertiary in type.

Primary Alcohol - the hydroxyl group is bonded to a carbon atom

that is bonded to only one other carbon atom.

Secondary Alcohol - the hydroxyl group is bonded to a carbon atom

that is bonded to two other carbon atoms.

Tertiary Alcohol - the hydroxyl group is bonded to a carbon atom

that is bonded to three other carbon atoms.

As well, depending on the number of hydroxyl groups contained within alcohol molecules,
the following prefixes are required.

One -OH’s ol
Two -OH’s diol
Three -OH’s triol
Four -OH’s tetrol

Examples
Formula # hydroxyl groups (other) Alcohol Name
two hydroxyl groups 1,2 - ethandiol
HO OH
2 carbon HC chain

OH three hydroxyl groups 2,2,3 - butantriol

HO 4 carbon HC chain
HO

6
Examples

Formula # hydroxyl groups (other) Alcohol Name

ethanol

HO

one hydroxyl group 2 - propanol

OH 3 carbon HC chain

1,2 - propandiol
OH
HO

two hydroxyl groups 2,2 - propandiol

3 carbon HC chain

HO OH

7
 one hydroxyl group 2 - methyl -1- propanol
one methyl group or
3 carbon HC chain
OH 2 - methyl propanol

2 - butanol

OH

2,3,4 - pentantriol

OH OH

OH

8
 Chemistry 2202
Alcohols

Questions: Complete the following chart. Name: ____________________

Formula # hydroxyl groups Alcohol Name

# C in HC chain

2-methyl-2-propanol

1 hydroxyl group on C 1
4 C chain

2,2-dimethyl-1-butanol

9
 2-butanol

Methyl on C 3
Hydroxyl on C 2

1-ethanol

10
Ethers
- two CH groups that are joined by an oxygen atom.
- basic formula: R-O-R
where R - represents the parent carbon chain
O - represents the functional group

Properties
- highly flammable
- soluble in water
- liquids at room T

Examples
- Diethyl ether (C4H10O)(CH3 CH2 O CH2 CH3)
- used as an anesthetic for more than 100 years (until 1950s)
- flammable and causes nausea

Other Examples
Ether Common Use

C2H4O fungicide

C7H8O Perfume

11
C8H8O vanilla flavouring agent

C14H12O3 sunscreen ingredient

C15H20O3 sex pheromone in American cockroaches

C21H30O2 THC

C50H70O14 marine neurotoxin secreted by dinoflagellates; “red tides”

12
Naming Ethers
1. Name each C-H chain using the longest alkyl (CH) group as the parent chain.
If 2 chains same - add prefix “di.”
If 2 chains different - list in alphabetical order as one word.
2. Add the word ‘ether’ to end.

Examples
dimethyl ether
CH3 O CH3

ethylpropyl ether
O

O ethylmethyl ether

diethyl ether

13
 dipropyl ether

dipentyl ether

methylpropyl ether
O

ethylpropyl ether

butylethyl ether

14
 Chemistry 2202
Worksheet 1: Alkyl Halides, Alcohols and Ethers

Name:____________________

Instructions: Complete the following chart.

Structural Diagram Compound Type Compound Name

2,2-dimethyl-4-propyl-
3-heptanol

2 2,2-dibromopropane

15
3

2-methyl-1-butanol

OH

OH

3-chloro-2,4-
difluorooctane

16
6

dimethylether

OH

17
9

butylpentylether

10

Cl F

18
Amines
- an organic compound formed from the decomposition of amino acids by bacteria.
- compounds smell like rotting fish, and other peculiar generally disagreeable odours
-also cadaverine, or rotting flesh(NH2(CH2)5 NH2)
-derivatives of ammonia NH3
-found commonly in nature
- basic formula is R-NH2 where R represents parent carbon chain
NH2 represents functional group

Properties
-usually polar molecules
-miscible in water
-solubility decreases with length of parent chain

Naming Amines
1. Count the number of carbon atoms in the chain & use appropriate prefix.

2. Name as an amine by dropping ‘e’ and adding ‘amine’ to the name.

Examples
methanamine
NH2

ethanamine

NH2

hexanamine
NH2

propanamine

NH2

NH2 butanamine

nonanamine
NH2

NH2 heptanamine

19
Amide
-these compounds can be found in protein molecules
-are the peptide bonds that join amino acids to each other
-basic formula R = O where R represents the parent chain
O and NH2 represent the functional group
NH2
(carbon atom double bonded to an O atom & single bonded to an N group)

Properties
-usually polar molecules
-polar end is soluble in water
-solubility of molecule decreases with increasing length of parent chain

Examples
-Acetaminophen - pain killer
-Urea - first organic compound produced synthetically
- found naturally in mammal urine

Naming Amides
1. Count the number of carbon atoms in the parent chain and use appropriate prefix.

2. Name as an amine by dropping ‘e’ and adding ‘amide’ to the name.

Examples
ethanamide

methanamide

butanamide

hexanamide

nonanamide

octanamide

20
 Chemistry 2202

Worksheet 2: Amines and Amides Name:____________________

Instructions: Complete the following chart.

Structural Diagram: Structural Diagram:

Name: 2-hexanamine Formula: CH3 (CH2)4CO(NH2)

Name:
Structural Diagram: Structural Diagram:

CH3CH2CH(NH2)CH3
Name: 4-nonanamine Name:

Structural Diagram: Structural Diagram:

Name: methanamide Name: cyclopentamine

Structural Diagram:

Name: hexanamide

21
Aldehydes

- an organic compound with a double bonded oxygen atom on the end carbon of a
carbon stem
- the functional group is the oxygen atom (carbonyl group)
- the basic formula is:
R=O where R represents the parent chain
O represents the functional group

Examples
Methanal (CH2O)
- common name “formaldehyde”
- historically used to preserve biology specimens
-currently used to preserve bodies
- causes cancer and mutations in animals
- methanol becomes methanal in body

Ethanal (C2H4O)
- ethanol becomes ethanal in the body
- “hangover” - headaches, vertigo, gastric upset

Naming Aldehydes
1. Identify longest C chain and use prefix.
e.g. 1 C - meth
2. Replace ending -e with -al.
e.g. methane –> methanal

Examples
O ethanal

O hexanal

O 3-methylbutanal

O
methanal
CH2

22
Ketones
- an organic compound with a double bonded oxygen atom on any carbon within the
parent carbon chain.
- functional group is oxygen atom within the molecule
- the basic formula is

R-C-R where R represents the parent chains

O represents the functional group
O

Examples
- Propanone (CH3COCH3)
- common name “acetone”
- solvent in nail polish remover, varnish, plastic cement

Naming Ketones:
1. Identify longest C chain and name with prefix
e.g. 3 C - prop
2. Indicate the position of the carbonyl group
3. Replace ending -e with -one.
e.g. 2 - propanone

Examples
O propanone

O 2 - butanone

3 - hexanone

4 - heptanone
O

O
4 - octanone

23
 Chemistry 2202

Worksheet 3: Aldehydes and Ketones Name:____________________

Instructions: Complete the following chart.

Structural Diagram Compound Type Compound Name

heptanal

2
O

3
3-methylpentanal

24
5 2,2-dimethyl-4-octanone

O
6

7 4,4-diethylhexanal

9 3-ethyl-2-pentanone

10

25
Carboxylic Acids
(a.k.a. Organic Acids)

- an organic compound with a double bonded oxygen atom and a hydroxyl (OH) group
at the end of a parent carbon chain. -
- functional group -COOH
- basic formula

where R represents the parent chain

COOH represents the functional group
(aka carboxyl group)

Properties
- polar, H-bonds, acidic
- sour, tangy taste
- strong odours
- found in citrus fruit, crabapples, rhubarb

Examples
- Methanoic Acid (HCOOH)
- common name “formic acid”
- irritant in bee/insect stings
- used to remove hair from animal hides

- Ethanoic Acid (CH3COOH)

- common name “acetic acid”
- produced when wine turns sour
- pungent odour in vinegar

- Butanoic Acid (CH3CH2CH2COOH)

- rancid butter, dirty feet smell
- police dogs follow carboxylic acid in sweaty feet

- Octanoic Acid
- common name “stearic acid”
- extracted from beef fat
- used to make cheap wax candles

26
Naming Organic Acids
1. Name the C chain with prefix.
e.g. 3 C - prop
2. Change -e to -oic acid.
e.g. propane - propanoic acid

Examples
O
propanoic acid
OH

O
butanoic acid
OH

OH
pentanoic acid
O

O
octanoic acid
OH

O
methanoic acid
OH
heptanoic acid
OH

HO
hexanoic acid
O

27
Esters
- an organic compound with a double bonded oxygen atom and a single bonded oxygen
atom in the middle of a parent carbon chain.
- formed by reacting an carboxylic acid with an alcohol
- the basic formula is
R–C-O-R where R-C=O represents acid side
O-R represents alcohol side
O

Properties
- many esters have pleasant aromas and flavours
- found naturally in fruits and flowers
- used in foods, cosmetics, perfumes, synthetic fibers, and solvents

Examples
Chemical Formula Compound Name Use

C5H10O2 methyl butyrate apple aroma

C5H10O2 n-propyl acetate pear aroma

28
C6H8O6 methyl salicylate wintergreen

C7H12O2 ethyl propionate rum aroma

C7H14O2 isoamyl acetate banana,

C9H8O4 ethyl acetate fingernail polish remover

C10H12O2 ethyl phenylacetate honey aroma

C10H20O2 octyl acetate orange aroma

29
Naming Esters
- We separately name the acid (=O) side and the alcohol side (-O with H dropped from
OH to allowing bond with carbon from acid side)

1. Name C chain from alcohol (side with C-O) like a branch

e.g. 3 C –> propyl
2. Name C chain from acid (side with C=O), but change ending -e to -oate
e.g. 2 C –> ethane –> ethanoate
3. Combine both parts
propyl ethanoate

Examples
propyl propanoate
O
O

propyl ethanoate
O

methyl butanoate
O

methyl octanoate

O ethyl ethanoate
O

propyl methanoate

30
 Chemistry 2202
Worksheet 4: Carboxylic (Organic) Acids and Esters

Name:____________________

Instructions: Complete the following chart.

Structural Diagram Compound Type Compound Name

1 butanoic acid

OH
2
O

3 2,4-dimethylheptanoic acid

O
4
OH

31
5 butylpentanoate

O
6
O

7 propyl methanoate

O
8
O

9 benzoic acid

10 O

32
 Chemistry 2202
Worksheet 5: Amines, Amides, Aldehydes, Ketones, Organic Acids and Esters
Name:________________________

Instructions: Name each structure below, then identify the type of hydrocarbon derivative that it is.
1 2

O
NH2

Type: __________________________ Type: __________________________

Name: __________________________ Name: __________________________

3 4

OH
O
O
O

Type: __________________________ Type: __________________________

Name: __________________________ Name: __________________________
5 6

O O

NH2

Type: __________________________
Type: __________________________
Name: __________________________
Name: __________________________
7 8

OH O

Type: __________________________ Type: __________________________

Name: __________________________ Name: __________________________
9 10
NH2
O

Type: __________________________ Type: __________________________

Name: __________________________ Name: __________________________

33
 Chemistry 2202
Worksheet 6: Hydrocarbon Derivatives Review
Name:____________________

1. Complete the following chart by writing the name of the compound.

1 2
O
OH O

Name:___________________________ Name:___________________________
3 4

HO
O O

Name:___________________________ Name:___________________________
5 6
O Cl
Br

Name:___________________________
Name:___________________________
7 8
NH2
NH2
O
Name:___________________________ Name:___________________________

9 10
Cl F
OH
Br

Name:___________________________ Name:___________________________
11 12
O HO

OH OH
Name:___________________________ Name:___________________________

34
2. Complete the following chart by drawing the structural formula of the compound.
1 2

1-propanol methyl propyl ether

3 4

3-decanone 1,2-difluoropropane
5 6

propyl methanoate 2-pentanol

7 8

ethanal propanoic acid

9 10

2-bromopropane 2-pentanol
11 12

butanal 2-methylpentanoic acid

13 14

dimethyl ether methyl ethanoate

35
 Polymerization

Polymerization
- The process of joining monomers to form polymers.

- Monomers - small carbon based molecules that combine like links in a chain that
can be joined to form polymers

- Polymers - literally means many parts

- macromolecules
- can be composed of thousands of monomers
- can be composed of multiple types of monomers
-found in oils, tars, resins, rubber, plastics, etc.

-Two main methods:

1. Addition Polymerization
2. Condensation Polymerization

1. Addition Polymerization
-Occurs when unsaturated monomers join together to form polymers
-The double or triple bond of the unsaturated compound is broken and the
individual molecules join together.

General Equation

Monomer + Monomer + H2 ----> Polymer

Example 1: Polymerization of ethene to produce polyethylene

Example 2: Polymerization of ethene and propene

36
2. Condensation Polymerization
-Occurs when two different types of monomers join together to form
polymers.
-monomers contain a hydroxyl functional group.
-Water is condensed as a product out of the reaction.
-Monomers bond at site where atom is removed.

General Equation

Organic Acid + Alcohol ----> Polymer +Water

Example:

37
Natural Polymers
-Carbohydrates
-sugars; used for energy
-photosynthesis

6CO2 + 6H2O —> C6H12O6 + O2

glucose

Glucose - main type of sugar produced during photosynthesis

- stored in animals as glycogen
- stored in plants as cellulose and starch
- polymers of glucose are called polysaccharides

-Cellular respiration - reverse polymerization

-Proteins

-composed of amino acids

-polymers used for cell and muscle structure
-examples include hormones, enzymes, muscles, hair, ligaments, antibodies,
etc.
- vital for the normal functioning of the body
-used to transport nutrients throughout the body
-used to help the body fight diseases, etc.

-Lipids
-composed primarily of long chain saturated fatty acids
-major building blocks of cell membranes in animal(human) bodies
-used to regulate our metabolism
-used by the body to store energy

Synthetic Polymers
- often referred to as plastics
- most, however can be categorized into three main categories
1. thermoplastics - generally elastic and flexible
- turns to liquid when heated
- freezes to a glassy state

2. thermosets - materials that irreversibly cure

- curing process transforms polymer
- examples include vulcanized rubber, epoxy

3. elastomers - polymers with high elasticity properties

- material has ‘memory return’ capability
- examples include natural rubber
38
Chemistry 2202

Unit 3: Hydrocarbon Derivative Reactions Name:_________________

Recall: Pure Hydrocarbon Reaction Types

1. Cracking
2. Reforming
3. Addition
4. Substitution
5. Complete Combustion
6. Incomplete Combustion

Now: Hydrocarbon Derivative Reactions Types

7. Elimination
8. Esterification

Type 7 : Elimination
-Elimination reactions take place between organic halides (R - X) and alcohols(R -
OH).
-It is the opposite of an addition reaction in that alkenes and alkynes are the
products when X and OH are removed from the organic halides or alcohols.

Two Subtypes:
-Organic Halide Elimination
-Alcohol Elimination

39
Sub-Type 1: Organic Halide Elimination

General Equation

R-X + OH- —> R + HOH + X-

organic halide alkene halogen ion
alkyne

Example 1: Elimination of 2-bromopropane

Example 2: Elimination of 3-iodohexane

Sub-Type 2: Alcohol Elimination

-alcohol elimination reactions requires a catalyst (ex: sulfuric acid)

General Equation

R - OH ------> R + HOH
alcohol acid alkene
alkyne

Example 1: Elimination of ethanol

Example 2: Elimination of 3-pentanol

Chemistry 2202

40
Questions: Complete the following chart. Name: ____________________

1. Write elimination reactions for each of the following organic halides.

1. 3-chlorohexane

2. 2-bromobutane

3. 4-iodononane

2. Write elimination reactions for each of the following alcohols.

1. 1-butanol

2. 3-hexanol

3. 2-pentanol

3. Complete the following elimination reactions using structural formulas.

1. 2-pentanol ---->

2. 3-chloroheptane + hydroxide ion

41
Type 8: Esterfication

-Esterfication reactions take place between organic(carboxyl) acids and alcohols.

-The result is the formation of an ester and water
-The hydroxyl group from the organic acid joins with the hydrogen atom from the
alcohol to form a water molecule.

General Equation

Organic Acid + Alcohol ------> Ester + Water

Example 1: methanoic acid + ethanol

Example 2: propanoic acid + 1-pentanol

42
 Chemistry 2202

Questions: Complete the following chart. Name: ____________________

1. Write esterfication reactions for each of the following.

1. methanoic acid + methanol

2. propanoic acid + 1-ethanol

3. butanoic acid + 2-butanol

4. ethanoic acid + 2-propanol

5. hexanoic acid + 2-butanol

2. Fill in and Name the missing reactant in each of the following esterfication reactions.
1.

2.

3.

43