Carboxylic Acids, Esters, Ethers, Amines

Are you still surviving? Is organic chemistry making your blood boil? 

NO FEAR. BERYLLIUM CHEMISTS ARE HERE!

Last post, we talked about some of the basic functional groups that you may come across. Today, we will teach you some more complex functional groups! (Yay or nay?) Don't understand the basics yet? Refer to the posts below!

Carboxylic Acids

R - functional group with one valence electron

• Acidic; can be neutralized with a base
• Compounds that contains the carboxyl functional group -COOH (a double bonded O and an OH) at the end of the chain
• Methanoic acid is the simplest acid
• Start counting from the side with the carboxyl functional group

NAMING: At the end of the main chain name, drop the "e" and add "-oic acid"

Example: Acetic acid (Ethanoic acid)

How to draw it? First start off with your basic -COOH structure. We know that ethane means two carbons, so just attach another carbon to the structure. (Remember the octet rule for bonding - three hydrogens would be bonded to the carbon!)

Another example: Name this acid

1. The longest chain of carbon is 3. The ending of the name would be 'propanoic acid'.
2. Counting from the carboxyl functional group, we find that there are two methyl's at the location "2" and one bromo at "3".
3. Putting it in alphabetical order, the name of this acid would be: 3-bromo-2,2-dimethylpropanoic acid.

Esters

• formed by combining a carboxylic acid with an alcohol functional group
• Oxygen separates the 'alcyl' and 'alkyl' group
• can be easily converted back into its original states
• has a fruit odour 

NAMING: When naming, the alkyl group is named first and has an '-yl' ending. When naming the acyl group (carboxylic acid), remove the '-oic acid' and replace it with '-oate'

Example: 

1. Count the alkyl chain first. The longest chain consists of 5 carbons, so it is named 'pentyl'.
2. Now looking at the acyl group, the longest chain has four carbons - 'butanoate'.
3. Put it all together and you have: pentyl butanoate!

Ethers (EE-THERS)

• The main difference between ethers and esters is that there is no double-bonded oxygen
• Ethers are side groups: Oxygen starts the side group and is connected to two alkyl chains
• has a pleasant odour, highly flammable, colorless, insoluble in water, and acts as good solvents

NAMING: Ether + Alkane

Same procedure as before, except the endings for ethers are '-oxy'.

Example: 

Can you try to guess what the name of this ether is? If you guessed 1,1-dimethoxyethane, good job! There are two ether side groups containing methyl located at the first carbon, and the longest chain is two.

Give this one a try: 2-methoxy-2,2-dimethylethane

(The answer will be at the bottom of this post)

We are almost through... Bear with me!

Amines!

• functional group that has Nitrogen bonded to 3 Hydrogens or Carbons
• it is a side group
• related to ammonia (NH3)
• has a "fishy" odour
• soluble
• They're organic bases that can easily form salts when reacted with acids (through neutralization of course!)

NAMING: Side group + "amino" + parent chain

Standard naming rules, but the alkyls attached to the Nitrogen is followed by "amino". (Eg. methylamino)

Example: 2-aminopentane

Here is the solution to 2-methoxy-2,2-dimethylethane!

Whew, too much chemistry for one night. Off to bed!