2.3 Functional Groups and Complex Organic Compounds

Bees live in highly organized communities called-

• Colonies

What are some examples of plants that are pollinated by bee colonies?

• Beans

• Squash

• Cucumber

• Coffee trees

• Cacao trees

• Apples/oranges/grapes

Name the 3 types of bees

1. Worker

2. Queen

3. Drone

A bee colony (or hive) is controlled by who?

• One female bee- the queen

What is the role of the Queen Bee?

• She produces chemical signals that controls the behaviour of the bee colony

What are the Queen’s chemicals called?

• Queen Mandibular Pheromones

What is a cool chemical thing about the Queen’s pheromones?

• The existence of a tiny functional group containing a double bond or an oxygen atom

• It can modify the behaviour of an entire colony of bees

What are some things the Queen pheromones can make the other bees do?

• Maintaining the hive

• Causing a swarm

• Mating

• Birth control for female worker bees

The molecules in the Queen pheromones all include what?

• Carbon-to-Carbon bonds

• Carbon-to-Hydrogen bonds

• Oxygen bonded to Carbon with a single or double bond

When a Carbon is bonded to a Hydroxide ion (OH^-), the molecule is classified as a what?

• An alcohol

In the alcohol molecule, the Hydroxide ion is called what?

• A Hydroxyl group

A molecule classified as an alcohol has what?

• One Carbon atom bonded to an Oxygen atom through a single bond

A molecule classified as an ether as what?

• Two Carbon atoms bonded to an oxygen atom with single bonds

Is this an alcohol or an ether?

• Alcohol

Is this an alcohol or an ether?

• Ether

When bonding, if Oxygen has two pairs of non-bonding electrons, what happens to the molecule?

• It’s bent

How do the molecules of water, methanol, and dimethylether look similar?

• Alcohol: one Hydrogen atom → hydrocarbon chain

• Ether: both Hydrogens → two hydrocarbon chains

What is the name of the specific alcohol in wine?

• Ethanol

Describe fermentation for wine

• Yeast digests sugar in a solution

• CO₂ is a byproduct; ethanol is a byproduct

We’ve already learned that Ethyl is two Carbon atoms which is the same in this lecture for-

• Ethanol

• Has 2 Carbons

How do you name alcohols?

• Similar to Hydrocarbons we already learned

• Alkanes: -ane ending is chaned. -an stays but e become -ol

When alcohols contain more than one alcohol functional group, what are they called?

• Polyalcohols

When naming polyalcohols, what must you remember?

• To add di/tri befor the -ol ending

How many subclasses of alcohols are there? What are their names?

1. Primary

2. Secondary

3. Tertiary

How are alcohols subclassified?

• According to the type of Carbon atom the -OH group is bonded to

Describe primary alcohols

• -OH group is bonded to a Carbon atom that is bonded to only one other Carbon atom

Describe secondary alcohols

• -OH group is bonded to a Carbon atom that is bonded to two other Carbon atoms

Describe tertiary alcohols

• -OH group is bonded to a Carbon atom that is bonded to three other Carbon atoms

What is an anesthesiologist?

• Someone who administers a safe and appropriate dose of an anesthetic to relieve pain or render someone unconscious during surgery

Describe the first documented use of a surgical anesthetic

• Boston, 1844

• A dentist administered Nitrous Oxide (N₂O) for a tooth extraction

What is diethylether?

• Organic compound whose effects lasted longer than N₂O

• BUT caused vomiting

• Used today as a solvent for fats/oils

An ether is a class or organic compounds where an Oxygen is attached to-

• Two alkyl groups

If an ether has Oxygen in it, how can you think about the chain?

• The Oxygen atom divides the ether molecule’s Carbon chain into two halves

How do you name ethers?

• Attach the suffix -oxy to the name of the shortest chain that flanks the Oxygen atom

• The longest chain becomes the parent chain

Just like water, alcohols and ethers are-

• Polar solvents

Do alcohols and ethers become more or less polar as the number of Carbon groups in their chains increases?

• Less polar

_____ _____ is the primary force responsible for the attraction that occurs among alcohol molecules

• Hydrogen bonding

As a result of Hydrogen bonding, the boiling point of an alcohol is _____ than that of an alkane with a similar number of Carbon atoms

• Higher

Ethers lack the _____ _____ _____ and are therefore unable to form Hydrogen bonds the way water and alcohols can

• Hydroxyl functional group

What is this?

• A carbonyl functional group

Aldehyde and Ketone functional groups are based on a _____ _____ _____

• Carbonyl functional group

Aldehydes and Ketones have at least one _____ _____ . Which is what?

• Carbonyl group

• A Carbon atom double-bonded to an Oxygen atom

Describe the main difference of Aldehydes from Ketones?

• An Aldehyde’s Carbon in the Carbonyl group has one Carbon on one side and one hydrogen on the other

Describe the main difference of Ketones from Aldehydes?

• A Ketone’s Carbon in the Carbonyl group is flanked on either side by Carbons

An Aldehyde parent chain begins where? Where does it terminate?

• Parent chain begins with the Carbon atom that is double bonded to Oxygen

• Terminates in a single Hydrogen atom

When naming Aldehydes, what does the ending become?

• -al

• Alkane -ane ending but remove the -e and replace with -al

Ketones are similar to Aldehydes except where is the Carbonyl group?

• In the middle

• (found at the end for Aldehydes)

For naming Ketones, what does the ending change to?

• -one

• Keep -an from Alkanes and change -e to -one

Aldehydes and Ketones have _____ boiling points than alcohols with a similar number of Carbon atoms. Why?

• Lower

• Both lack the Hydroxyl group so they can’t form Hydrogen bonds

Aldehydes and Ketones have a Carbonyl group and the presence of this group makes the molecules quite _____

• Polar

The presence of the Carbon chain gives longer-chained Aldehydes and Ketones the ability to do what?

• To dissolve non-polar substances

• i.e. they are good solvents!

Why when you overdo exercise do you feel muscle cramps and a sharp pain in your abdomen?

• Because your body is producing lactic acid more quickly than it can be removed

How does this lactic acid buildup occur?

• Need energy for exercise

• Body converts glucose in your blood into usable energy and lactic acid

• Accumulation of lactic acid occurs when your cells lack enough oxygen to complete cellular respiration

What is a quick way to end cramps and abdominal pain? Why does this work?

• Stop the exercise, breathe for a short time

• Your body now has enough oxygen to complete cellular respiration which naturally removes lactic acid

A Carboxyl group is a combo of what two other groups?

• Carbonyl and Hydroxyl

Compounds containing a Carboxyl group are classified as what?

• As Carboxylic Acids

What is the simplest carboxylic acid? What is it used for today?

• Methanoic Acid (formic acid)

• Used as a preservative

• Used in coagulating and recycling latex and rubber

How do you name carboxylic acids?

• -an from -ane ending remains

• -e gets replaced with -oic acid

Carboxylic acids have _____ boiling points than the similar Alkanes

• Higher

Are carboxylic acids polar or non-polar?

• Polar

As with other polar organic compounds, the solubility of carboxylic acids _____ as the size of the Carbon chain increases

• Decreases

Esters also contain a carboxyl group BUT how has it been changed?

• Instead of a Hydrogen atom bonded to an Oxygen atom (-OH), the Oxygen atom is bonded to another Carbon chain

Esters with low molecular weight are easy to synthesize and are commonly used to enhance what?

• Fruit drinks

• Fragrances

• Artificial flavours

What is the ending for esters?

• -oate

What are the two parts to name an ester?

1. The alcohol-derived part

2. The parent chain

Absence of the Hydroxyl group causes esters to be _____ _____ than similar carboxylic acids and in turn also _____ _____

• Less polar

• Less soluble

Esters have _____ boiling points when compared to similar carboxylic acids

• Lower

The Amine functional group can be found in complex biological molecules like _____ and _____

• DNA

• Proteins

Amine functional group contains what element? That element is bonded to what?

• Nitrogen

• At least one Carbon atom/Carbon chain

When are DNA and proteins broken down into Amines?

• When living organisms die and decompose

What hormone is also an amine?

• Adrenaline

Amines can cause specific odours like-

• Ur!ne

• Decaying fish

Amines are subclassified according to what?

• The number of Carbon-to-Nitrogen bonds that are present

• Primary, secondary, tertiary

• (bonded to one Carbon, two Carbons, three Carbons)

What is the suffix for amines?

• -amine

The presence of the Nitrogen atom allows amines to have _____ boiling and melting points than similar sized hydrocarbons

• Higher

Smaller amines are _____ _____ in polar solvents like water

• Readily soluble

Nitrogen atoms have _____ electronegativity

• High