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Functional Groups By Dr. Christophy Functional Groups • “Arrangements of atoms in an organic compound that is capable of characteristic chemical reactions.” • Functional groups contain at least one atom that is not C or H, usually O or N or a halogen. • R is used to represent a carbon/hydrogen chain. R’ is used to represent a chain that may be different on the same molecule. Alkyl Halides • Hydrocarbon in which a halogen is attached to a carbon chain. • The halogen is named as a substituent group, just like ethyl or methyl. • The halogen names are fluoro-, chloro-, bromo- and iodo- Naming Examples – Alkyl Halides Name this structure: Name this structure: Cl H3C H2 C C H Br CH3 H3C H2 C C H H C CH3 Br Click here to see the answer Click here to see the answer Alcohols • An alcohol contains an “OH” group attached to a hydrocarbon. OH CH R R' Alcohols (cont.) • Alcohols all have the ending “-ol”. • A number indicates to which carbon the functional group is attached. The alcohol gets the lowest number possible. • Example: OH CH H3C 2-propanol CH3 Naming Examples - Alcohols Name this alcohol Name this alcohol: OH H2 C H3C OH H2 C CH C H2 CH CH3 CH3 OH CH H3C CH C H2 CH3 Click here to see the answer Click here to see the answer Types of Alcohols • If the alcohol is attached to a carbon that is also attached to two hydrogens and one other carbon, that is a primary alcohol. • If the alcohol is attached to a carbon that is also attached to one hydrogen and two other carbons, that is a secondary alcohol. • If the alcohol is attached to a carbon that is also attached to no hydrogens just three other carbons, that is a tertiary alcohol. Types of Alcohols (cont.) Identify the following as primary, secondary and tertiary alcohols: OH H2 OH C CH H3C C H2 H3C CH3 H2 C H3C Click for the answer CH3 OH C CH3 Ethers • When the hydrogen in an alcohol is instead replaced by a hydrocarbon group, the result is an ether: R O R' The R groups may be the same or different Naming Ethers • Ethers are named by naming the hydrocarbon on either side of the oxygen. • The R-group names are placed in alphabetical order. • If the R-groups are the same, the prefix “di” is used. • The last word in the name is “Ether” Naming Examples: Ether H2 C H3C O H2 C CH3 Click here to see the name H3C H2 C O H2 C H2 C Click here to see the name CH3 Ketones • A ketone, like an alcohol, has a carbon attached to an oxygen. This time, however, the C and the O are connected by a double-bond. • The C=O group is called a “carbonyl” group O C R R' Naming Ketones • The suffix for a ketone is “-one” • Ketones are named the same way as any other hydrocarbon, except the longest chain must contain the C=O group, and the final “e” on the end of the name is replaced by “-one” • Number the carbon that contains the double-bonded “O” with the lowest number possible. Naming Examples - Ketones O H3C H2 C C CH CH3 C H2 Click here to see the name CH3 O H2 C C H3C CH3 CH Click here to see the name H2C CH3 Aldehydes • Aldehydes are ketones at the end of a chain. O R CH • The ending for an aldehyde is “-al” • Since the carbonyl group is always at the end, there is no need for a number. Naming Examples O O H2 C H3C H2C CH Click here to see the name H2C CH CH2 H3C Click here to see the name O H3C CH Click here to see the name Carboxylic Acids • Carboxylic Acids are kind of a combination of an aldehyde and an alcohol. O R C O H Naming Carboxylic Acids • The ending is always “-oic acid” • Again, no number is needed because the group is always at the end. Carboxylic Acid Examples O H C O H Click here to see the name O H3C H2 C H2 C C O Click here to see the name H Esters • Esters are a combination of a ketone and an ether • The general formula is: O R C O R' Naming An Ester • Esters are just a little tricky to name. • The name of the group AFTER the “O” is first. • The second word in the name is the part that includes the carboxyl group and ends with “oate” Naming Examples - Ester O H3C H2 C C O CH3 Click here to see name O H3C H2 C H2 C H2 C C O Click here to see name H2 C CH3 Amines • Amines contain a nitrogen attached to a carbon and one or more hydrogens • Like alcohols, amines can be primary, secondary or tertiary. R R' N R" Any of these R groups could be a hydrogen Amides • An amide is attached to a carbon that has a carbonyl group. O C R H N R'