Hydrocarbon Derivatives

-Alcohols-Haloalkanes-Aldehydes-Ketones-Carboxylic Acids-Esters-Ethers-Amines-Amides

Hydrocarbon Derivatives

• These are organic compounds that are based on hydrocarbons with the addition of specific functional groups

• A functional group is a reactive group of atoms (eg. –OH)

• Due to the reactivity of the functional groups, we can determine the physical and chemical properties of compounds

• We also classify compounds based on these groups

• We will now explore six groups of hydrocarbon derivatives

ALCOHOLS

Alcohols

• An organic compound containing the hydroxyl, –OH, functional group

• Have the general formula of R—OH

• The “R” represents the alkyl group

• Example:

CH3—CH2—OH

Naming Rules

1. Locate the longest carbon chain (must contain the carbon attached to the –OH group.) Name the parent alkane

2. The suffix is –ol; indicate the position of the –OH group in front of the suffix

3. More than one –OH group; use di, tri, tetra and keep entire root name

4. Number the chain so that the –OH group has the lowest number

5. Add a position number before the name of the root to indicate the position of the –OH group

6. Name and number any branches (as you would for alkanes)

7. Put it all together: branches + root

Try it!

• Name this alcohol:

CH3—CH2—CH2—OH

CH3—CH—CH2—CH2—CH3

|

OH

One more...

• Name this alcohol and state whether it is primary, secondary or tertiary.

CH3—CH—CH2—CH2—CH3

|

OH

Draw:

3,4-dimethylhexan-2-ol

Butane-1,3-diol

Three classes of Alcohols

• Primary Alcohol (1°) – the OH group is bonded to a carbon that is only bonded to one other carbon

• Secondary Alcohol (2°)– the OH group is bonded to a carbon that is bonded to two other carbon atoms

• Tertiary Alcohol (3°)– the OH group is bonded to a carbon that is bonded to three other carbon atoms

Physical properties of alcohols

• Polar or non-polar?

• Boiling points? Intermolecular forces?

Haloalkanes

• HCs with at least one halogen atom

• Basic structure R-X, where R is the root and X can be F, Cl, Br, I

• Often result of substitution reactions

• Eg. Chloroform, CFCs (refrigerants & propellants)

Naming haloalkanes

1. Identify the root – longest continuous chain

2. Identify the suffix – which family

3. Type of halogen (F-fluoro, Cl-chloro, Br-bromo, I-iodo); more than one – di, tri, etc

4. Halogen gets the lowest number

5. Then look for alkyl groups

6. .Halogen substituent groups and alkyl side groups are arranged alphabetically

Try these…

• CH3-CH2-CH2-Cl

• CH2=CH-CH2-Br

• Try #85-95 on page 49

Physical properties

• polarity/solubility in water?

• Boiling points?

ALDEHYDES

Aldehyde

• Contain a formyl group,

which is a carbonyl functional

group >C=O with a H bonded

to the C atom

Only one possible position – always C#1

• Have characteristic scents and tastes

• Example – Cinnamon or Formaldehyde, vanillin, cilantro

Naming Aldehydes

• As with other naming (ID root)

• The carbonyl group will always be on a terminal carbon, thus there is no need to give a position number

• Simply name the carbon chain; drop the –e from the end and add –al; give the C=O position 1

• Add branches (if any) as you have for all others!

Try Some

HC—CH2—CH2—CH3

CH3—CH2—CH—CH

Try page 52: #96-105

O||

O||

| CH2—CH3

Physical properties of aldehydes

• Polarity?

• Boiling points? Compared to alcohols?

KETONES

Ketones

• Contain the carbonyl group C=O

• Has an alkyl group on either side of the C=O

• General formula R-CO-R`

Naming Ketones

• Find the longest carbon chain containing C=O

• Number the chain so that C=O has lowest number

• Drop the final –e from the alkane name and add –one

• Name and add branches as you would for alkanes

Try These

CH3—CH2—CH2—C—CH3

CH3—CH—C—CH2—CH2—CH3

|

CH3

O||

O||

CARBOXYLIC ACIDS

Carboxylic Acids

• Contain a carboxyl group

—C—OH

• General formula of R—COOH

• Polar molecules

• Soluble in water

• Have high MP and BP

O||

Naming Carboxylic Acids

• Name the parent alkane; drop the –e at the end of the alkane name and add –oic acid

• Carboxyl group is always given position one (no need to state this!)

• Name any branches as we do for alkanes

Try some

CH3—C—OH

CH3—CH—CH2—C—OH

|

CH3

O||

O||

ESTERS

Esters

• Derivatives of carboxylic acids

• Contains the functional group

—C—O—

• General formula RCOOR`

• Example:

CH3—CH2—C—O—CH3

O||

O||

Naming Esters

• Choose the main part of the ester, containing the C=O group. Name this as the parent acid.

• Replace the –oic acid with –oate

• Name the second part of the ester as an alkyl group

• Put them together – alkyl group + parent acid

CH3—CH2—C—O—CH3

We would name this methyl propanoate

O||

Parent acid Alkyl Group

Try One

CH3—CH2—CH2—CH2—C—O—CH2—CH3

O||

ETHER

Ethers

• An organic compound that has two alkyl groups joined by an oxygen atom

• Has the general formula of R—O—R`

• R and R` indicate two alkyl groups

• The can be the same or different

• Example:

CH3—CH2—O—CH3

How do we get to this?

• You can think of alcohols and ethers as derivatives of water!

H—O—H Water

R—O—H Alcohol

R—O—R` Ether

Rules for naming Common Names

1. List the alkyl groups that are attached to the oxygen atom, in order of increasing length.

2. Place the suffix –ether at the end of the name

No numbers are needed to show the location of the oxygen atom!

Try it!

Name these ethers

CH3—CH2—O—CH2—CH2

CH3—CH2—CH2—CH2—O—CH2—CH3