Lab Activity: Functional Groups

Purpose: To construct models of organic molecules containing functional groups. To become more familiar with the IUPAC names for these compounds. To become more familiar with the shape and structure of these functional groups.

In each exercise, write the functional group in the square. Highlight or circle the functional groups in your structural diagrams

Part 1 - Alkyl Halides 1. Make a model of ethane. 2. Replace one of the hydrogen atoms with a chlorine atom. Name this molecule. Write the structural equation for this reaction and name the type of reaction.

3. Replace another hydrogen atom with a chlorine atom. There should be two isomers, draw and name them.

4. Make a model of bromo-chloro-iodoethane. Compare it with other models in the class. There should be many isomers. Draw and name the isomer that you constructed.

Part 2 - Alcohols: 1. Make a model of ethane. 2. Replace one of the hydrogen atoms with a hydroxyl group (-OH). Draw and name this molecule.

3. Use 4 carbon atoms, 10 hydrogen atoms, and 1 oxygen atom to make a model of an alcohol. There are 4 isomers, name and draw their structures. Classify each as primary, secondary, or tertiary alcohols. Part 3 – Ethers: 1. Make a model of methanol and a model of ethanol. 2. Place the two models next to each other so that the hydroxyl groups are facing. 3. Remove the hydroxyl group from one of the alcohols and the hydrogen atom from the hydroxyl group of the other alcohol. Now join the two molecules together. 4. Write down the structural equation for this reaction, name the products(s) and identify the type of reaction.

Part 4 – Aldehydes: 1. Make a model of ethane. 2. Remove two hydrogen atoms from one of the carbon atoms. Replace them with a double-bonded oxygen. Draw and name this molecule.

3. Make a model of propanal and draw it.

Part 5 – Ketones: 1. Use your model of propanal to create an isomer. Draw and name this molecule.

2. Make a model of pentanone. There are two isomers, name and draw their structures.

Part 6 – Carboxylic Acids 1. Make a model of ethane. 2. Remove all the hydrogen atoms from one carbon atom. Replace two of them with a double-bonded oxygen, and the third with a hydroxyl group. Draw and name this molecule. Part 7 – Esters: 1. Make a model of butanol and a model of methanoic acid. 2. Place the two models next to each other so that the hydroxyl groups are facing. 3. Remove the hydroxyl group from the alcohol and the hydrogen atom from the carboxylic acid. Now join the two molecules together. 4. Write down the structural equation for this reaction, name the products(s) and identify the type of reaction.

Part 8 – Amines: 1. Make a model of ethane and a model of an amino group (-NH2). 2. Replace one of the hydrogen atoms on ethane with the amino group. Draw and name this molecule. Classify it as a primary, secondary, or tertiary amine.

3. Build an isomer of the amine you made. Draw and name this isomer. Classify it as a primary, secondary, or tertiary amine.

Part 9 – Amides: 1. Make a model of ethane. 2. Remove all of the hydrogen atoms from one of the carbon atoms. Replace 2 of the hydrogen atoms with a double-bonded oxygen, and the third with an amino group. 3. Draw and name this molecule.

Check Your Understanding: 1. Define primary, secondary and teritary alcohols. 2. Ketones are isomers of what organic family? What is the difference between the two families? 3. What is the common name for propanone? Where might you find propanone in your daily life? 4. What is the common name for ethanoic acid? Where might you find ethanoic acid in your daily life? 5. What two families react to form an ester? What family does the last part of the name come from? 6. What element is found in amines and amides but no other organic family? SCH4U: Organic Families Summary

Family Functional Example Structural Melting Boiling Polarity Types Solubility Group Formula Point Point of IM in Water (name + (oC) (oC) Forces formula) Alkane Propane

Alkene Propene

Alkyne Propyne

Alkyl 1-bromopropane Halide

Alcohol 1-propanol

Ether Methoxy-ethane

Aldehyde Propanal

Ketone Propanone

Carboxylic Propanoic acid acid

Ester Methyl ethanoate

Amine 1-propanamine

Amide propanamide

Consider the compounds listed above. A) Based on your understanding of intermolecular forces, explain the differences in boiling points between the different non-polar compounds. B) Explain the difference in boiling points between the different polar compounds. C) Based on your understanding of water solubility, categorize each compound as either: insoluble, partly soluble or very soluble.