Orgo Chem - Aldehydes, Ketones, Carboxylic Acids, Esters, Amines and Amides

aldehyde

the carbonyl group is attached at the end of the parent chain

ketone

the carbonyl group is bound to a carbon which is bound to 2 carbon atoms in the carbon chain. For this reason, the simplest ketone is propanone.

carbonyl

a carbon double bonded to an oxygen; C=O

Naming Aldehydes

• Lowest address (number) to carbonyl carbon

• Base name will end in -al or -dial – we do not need to include a number because we know it is found at the end of the chain

• Follow the same naming rules as before for substituent chains in alphabetical order

naming Ketones

• Lowest address (number) to carbonyl carbon

• Base name will end in –one, -dione, -trione, etc. – address necessary since the carbonyl carbon can be anywhere in the chain

• Follow the same naming rules as before for substituent chains in alphabetical order

Carboxylic Acids

Organic family characterized by the presence of a carboxyl group –COOH

Naming Carboxylic Acids

• Count the carbon atoms and pick the longest chain that contains the carboxyl group

• Number the main chain such that the carboxyl group falls on carbon number one.

• Branches are named as before. • Name the main chain like it was an alkane but drop the ‘e' and add –oic acid

• Like alcohols and ketones, keep the ‘e’ if there is more than one.

• Carboxylic acids will never need a number as the COOH group will always be found on the end of the chain. HIGHEST PRIORITY!! You simply count the number of carbons like you would an alcohol and add -oic acid or -dioic acid to the end of the name.

Properties of Carboxylic Acids

• weak acids found in many foods

• Polar molecule

• capable of hydrogen bonding

• Similar solubility to alcohols

General form of an ester

Esters form from

the reaction of an acid and an alcohol

Naming Esters

• Identify the alkyl groups on either side of the functional group (note: the carbon in the C=O bond must be included in the alkyl group)

• Write the name of the alkyl group attached to the oxygen first, and the alkyl group attached to the carbonyl (C=O) second

• The first group named gets the –yl ending, the second group named drops the ‘e’ and gets the ending -oate

• Branches are named as before

Properties of Esters

• less polar than carboxylic acids because they do not contain the hydroxyl group

• Do not form hydrogen bonds

• Less soluble than carboxylic acids

• Smaller esters are gases at room temp, where larger ones can be waxy solids

amines

an organic fam made up of an ammonia (NH3) molecule that has one or more hydrogens replaces by alkyl (methyl, butyl, etc) or aromatic groups

properties of amines

• higher melting pts than similar sized hydrocarbons

• polar molecules w hydrogen bonding

three types of amines

• primary - one alkyl group

• secondary - 2 alkyl groups

• tertiary - 3 alkyl groups

naming amines

1. iden the longest alkyl group attached to the N which will be used for the ending and everything else will be considered a branch

2. other groups attached to the N are named by the same branch prefix but their location would be “N” and not a number since numbering is only for carbons

3. for the ending → use the alkane group but drop the e and replace w the location for the N and “amine”

4. however the “e” is left alone if there are multiple amine groups

benzene on amines

• if they are the main chain, they are called aniline

• if there are MORE THAN ONE BENZENE, they are referred to as phenyl

• and if they are not the main branch they are also referred to as phenyl

amides

an orgo fam of compounds with a carbonyl functional group bonded to a NH3 atom

properties of amides

• polar molecules

• made from carboxylic acids bonding to ammonia or amine groups

naming amides

1. iden the alkyl chain that contains the carbonyl group → would be the parent alkane

2. name the other chains attached to the N like branch chains

3. location is denoted with N for such branches

4. for the ending, drop the e and replace w amide

5. unless there are amide groups on both sides (“diamide”) so keep the e

Prefix for a carbonyl carbon is “ ____ if it is not the priority in the chain

oxo”