Hydrocarbon Derivatives: Carboxylic Acids, Esters,

Ethers, Amines and AmidesSCH4U 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 chainO Very polar (small carboxylic acids

soluble in water)O Form hydrogen bonds with one

anotherO Examples:

Naming carboxylic acids

O Identify the rootO Locate the longest chain that includes the

carboxyl carbon atomO 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 prefixO Name the compound

QuestionsO Name each carboxylic acid:

QuestionsO 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 acidO 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 waterO Cannot form hydrogen bonds with one

another (no –OH)O The product of a reaction between a

carboxylic acid and an alcohol

Naming estersO 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 acidO 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 chainO There is a space between the first and second part of the

prefixO Name the compound

QuestionsO Name each ester:

QuestionsO Draw the condensed structural

formula for each ester:O Butyl ethanoate

O Draw the line structural formula for each ester:O Ethyl 2-cyclobutylpropanoate

EthersO 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 anotherO Can form hydrogen bonds with water

molecules

Naming ethersO Identify the root

O Locate the longest chain (the R group) that is bonded to the oxygen atom

O Name the parent alkaneO 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 rootO If there are one or more alkyl side groups on the main

chain, name them as you would name any alkaneO Name the compound

O There is no space between the prefix and the root

QuestionsO Name each ether:

Drawing ethersO Identify the rootO Identify the alkoxy groupO Add any alkyl side groups on the

main chainO Add hydrogen atoms

QuestionsO Draw the condensed structural

formula for each ether:O MethoxyethaneO 3-ethoxy-4-methylhexane

O Draw the line structural formula for each ether:O 2-propoxybutaneO 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 nitrogenO Secondary amines: two carbon atoms bonded to the nitrogenO 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 anotherO All amines can hydrogen bond with water

Naming Amines O Identify the root

O Locate the longest chain that is bonded to the nitrogen atomO Name the parent alkane (drop the –e on the end)

O Identify the suffixO Number the carbon atoms in the main chain starting with the carbon

atom nearest the nitrogen atomO Indicate the position of the nitrogen atom if the main chain is three or

more carbon atoms longO Identify the prefix

O If the compound is a primary amine, there is no prefixO For secondary amines, write N, hyphen and the name of the smaller

alkyl groupO 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 compoundO There is no space between the prefix and the root

QuestionsO Name each amine:

Drawing aminesO Identify the rootO Identify the suffixO Identify the prefix O Add hydrogen atoms (nitrogen atom

has a total of three bonds)

QuestionsO Draw the condensed structural

formula for each amine:O MethanamineO Hexan-1,4-diamine

O Draw the line structural formula for each amine:O N-propylbutan-1-amineO N-ethyl-N-methylheptan-3-amine

Amides (suffix: -amide) O Contain a carbonyl group bonded to a

nitrogen atomO One or both of the hydrogen atoms on the

nitrogen atom can be replaced by alkyl groupsO 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 amidesO 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 suffixO 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 chainO Name any alkyl group bonded to the nitrogen atom the

same way with aminesO Name the compound

O There are no spaces between the prefix, root and suffix

QuestionsO Name each amide:

QuestionsO Draw the condensed structural

formula for each amide:O EthanamideO N,N-diethylhexanamide

O Draw the line structural formula for each amide:O 2-methylpropanamideO N-ethyl-N-propyl-2-methylbutanamide