Hydrocarbon Derivatives: Carboxylic Acids, Esters, Ethers, Amines and Amides SCH4U Spring 2012

Carboxylic acids (suffix: -oic acid) O Contain a carboxyl group (-COOH) O Made up of a carbonyl group with a hydroxyl group O Must always be on the end of a chain O Very polar (small carboxylic acids soluble in water) O Form hydrogen bonds with one another O Examples:

Naming carboxylic acids O Identify the root O Locate the longest chain that includes the carboxyl carbon atom O Name the parent alkane (drop the –e on the parent alkane) O Identify the suffix O There are no numbers in the suffix because the carboxyl group always involves carbon atom 1 O Identify the prefix O Name the compound

Questions O Name each carboxylic acid:

Questions O Draw the condensed structural formula for each carboxylic acid: O Butanoic acid O 3-methyl-4-phenylhexanoic acid O Draw the line structural formula for each carboxylic acid: O 4-ethyloctanoic acid O Pentandioic acid

Esters (suffix: -oate) O General formula: RCOOR’ O R represents any hydrocarbon or a hydrogen atom O R’ represents a hydrocarbon (contain at least one carbon atom) O Somewhat polar (-C=O) O Small esters soluble in water O Cannot form hydrogen bonds with one another (no –OH) O The product of a reaction between a carboxylic acid and an alcohol

Naming esters O Identify the root O Identify the part of the ester that contains the C=O group (comes from the acid) O Based on the name of the carboxylic acid O Name the parent carboxylic acid (drop the suffix of the acid) O Identify the suffix O Identify the prefix O First consider the part of the ester that is associated with the alcohol (ignore the oxygen atom and name only the alkyl group) O Name any side group on the main chain O There is a space between the first and second part of the prefix O Name the compound

Questions O Name each ester:

Questions O Draw the condensed structural formula for each ester: O Butyl ethanoate O Draw the line structural formula for each ester: O Ethyl 2-cyclobutylpropanoate

Ethers O An oxygen atom is single bonded to two carbon atoms O General formula: R-O-R’ (R and R’ are alkyl groups) O Slightly polar O Cannot form hydrogen bonds with one another O Can form hydrogen bonds with water molecules

Naming ethers O Identify the root O Locate the longest chain (the R group) that is bonded to the oxygen atom O Name the parent alkane O Identify the prefix O Number the carbon atoms in the main chain, starting at the end of the chain nearest the oxygen atom O Identify the alkoxy group (oxygen and shorter carbon chain) O To name the alkoxy group, identify the root of the shorter carbon chain then add –oxy to the root O If there are one or more alkyl side groups on the main chain, name them as you would name any alkane O Name the compound O There is no space between the prefix and the root

Questions O Name each ether:

Drawing ethers O Identify the root O Identify the alkoxy group O Add any alkyl side groups on the main chain O Add hydrogen atoms

Questions O Draw the condensed structural formula for each ether: O Methoxyethane O 3-ethoxy-4-methylhexane O Draw the line structural formula for each ether: O 2-propoxybutane O 2-phenoxyheptane

Amines (suffix: -amine) O Contain a nitrogen atom bonded at least one carbon atom (up to three) O Separated into three categories: O Primary amines: one carbon atom bonded to the nitrogen O Secondary amines: two carbon atoms bonded to the nitrogen O Tertiary amines: three carbon atoms bonded to the nitrogen O Any bonds that are not filled by a carbon atom are filled by a hydrogen atom O N-H bonds in primary and secondary amines are very polar O Primary and secondary amines can hydrogen bond with themselves and with one another O All amines can hydrogen bond with water

Naming Amines O Identify the root O Locate the longest chain that is bonded to the nitrogen atom O Name the parent alkane (drop the –e on the end) O Identify the suffix O Number the carbon atoms in the main chain starting with the carbon atom nearest the nitrogen atom O Indicate the position of the nitrogen atom if the main chain is three or more carbon atoms long O Identify the prefix O If the compound is a primary amine, there is no prefix O For secondary amines, write N, hyphen and the name of the smaller alkyl group O For tertiary amines, write an N in front of each of the smaller alkyl groups and order them alphabetically (if the two groups are the same, write N,N-di-) O Name the compound O There is no space between the prefix and the root

Questions O Name each amine:

Drawing amines O Identify the root O Identify the suffix O Identify the prefix O Add hydrogen atoms (nitrogen atom has a total of three bonds)

Questions O Draw the condensed structural formula for each amine: O Methanamine O Hexan-1,4-diamine O Draw the line structural formula for each amine: O N-propylbutan-1-amine O N-ethyl-N-methylheptan-3-amine

Amides (suffix: -amide) O Contain a carbonyl group bonded to a nitrogen atom O One or both of the hydrogen atoms on the nitrogen atom can be replaced by alkyl groups O Similar to amines, amides are separated into three categories: primary, secondary and tertiary amides O The product of a reaction between a carboxylic acid and ammonia or a primary or secondary amine O Can form hydrogen bonds with water

Naming amides O Identify the root O Determine the longest carbon chain that contains the carbonyl group O Name the parent alkane (drop the last –e) O Identify the suffix O Identify the prefix O Number the carbon atoms in the main chain (always start with the carbonyl carbon atom) O Name any alkyl side groups on the main chain O Name any alkyl group bonded to the nitrogen atom the same way with amines O Name the compound O There are no spaces between the prefix, root and suffix

Questions O Name each amide:

Questions O Draw the condensed structural formula for each amide: O Ethanamide O N,N-diethylhexanamide O Draw the line structural formula for each amide: O 2-methylpropanamide O N-ethyl-N-propyl-2-methylbutanamide