Hydrocarbon Derivatives: Carboxylic Acids , Esters , Ethers , Amines and Amides

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

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

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

4. Questions • Name each carboxylic acid:

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

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

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

8. Questions • Name each ester:

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

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

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

12. Questions • Name each ether:

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

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

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

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

17. Questions • Name each amine:

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

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

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

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

22. Questions • Name each amide:

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