6. Naming (& Drawing) Hydrocarbon Derivatives Part 1

• Functional Group Priorities


  The first step in naming a hydrocarbon derivative is to identify the highest priority functional group. This will determine the overall type of compound and will determine the suffix that will be used at the end of the name.
• Root of the name


  Comes from the number of carbons in the longest chain that contains the highest priority functional group
• Carboxylic Acid


  An organic compound that contains a carboxyl group (-COOH) at the end of the carbon chain

  
• Naming carboxylic acids


  1. Change the ending of the parent alkane name to -oic acid

  2. Since the carboxyl group has to be at the end of the carbon chain, no numbers are required to indicate its location
• Numbering for side groups in carboxylic acids

  The carbon atom in the carboxyl group is always #1

  
• Drawing a carboxylic acid


  1. Start with a carbon backbone of the appropriate length

  2. Add the double bonded oxygen and hydroxyl group to the last (or first) carbon

  3. Add the indicated side groups (remember to number from the carboxyl group)

  4. Fill in the hydrogens, giving each carbon a total of 4 bonds

  
• Ester


  An organic compound that contains a carbon that is double bonded to an oxygen and single bonded to an oxygen atom within a hydrocarbon chain

  
• Naming esters


  1. The name has two parts, separated by a space

  2. The first part comes from the alcohol and is named as an alkyl group - the name of the parent alkane, with the ending changed to -yl

  3. The acid name is then added, but with the ending changed from -oic acid to -oate
• Numbering for side groups in esters

  The carbon atom that is double bonded to the oxygen is always carbon #1

  
• Drawing an ester


  1. Start by creating a carbon backbone of the appropriate length for the acid portion

  2. Add the double bonded oxygen and single bonded oxygen to the last carbon

  3. Add the appropriate number of carbons to the single bonded oxygen, as indicated by the alkyl group name

  4. Add side groups, if any, to the acid portion

  5. Fill in the rest of the bonds with H, giving each carbon a total of 4 bonds

  
• Amide


  An organic compound that contains a carbon that is double bonded to an oxygen and single bonded to a nitrogen

  
• Naming amides


  1. The longest hydrocarbon chain containing the C=O group is considered the parent chain

  2. The ending of the parent alkane is changed to -amide

  3. For secondary and tertiary amides, the hydrocarbon chains bonded to the N are named as alkyl groups with an N- in front of them

  4. If there are two of the same group, N,N-di- is added to the alkyl group name

  5. If there are side groups on the parent chain, they are named in the same way as for other organic compounds, and the numbering starts at the carbonyl group

  
• Drawing an amide


  1. Start by creating the carbon backbone of the main chain attached to the -CON group

  2. Add the side groups to the main chain and the nitrogen as indicated by the name

  3. Fill in the hydrogens, giving each carbon a total of 4 bonds, and the nitrogen a total of 3 bonds

  
• Aldehyde


  An organic compound that contains a formyl group (carbon double bonded to oxygen and single bonded to hydrogen) at the end of a hydrocarbon chain

  
• Naming aldehydes


  1. Change the ending of the parent alkane name to -al

  2. Since the formyl group has to be at the end of the carbon chain, a number is not required to specify its location

  3. If there are side groups on the main chain, they are named and numbered in the same way as for hydrocarbons

  4. The parent chain must contain the formyl group and the carbon atom in the formyl group is always #1

  
• Drawing aldehydes


  1. Start with a carbon backbone of the appropriate length

  2. Add the double bonded oxygen to the last (or first) carbon

  3. Add the indicated side groups (remember to number from the formyl group)

  4. Fill in the hydrogens, giving each carbon a total of 4 bonds

  
• Ketone


  An organic compound that contains a carbonyl group (C=O) within a hydrocarbon chain
• Naming ketones


  1. Change the ending of the parent alkane name to -one

  2. When there is more than one possible position for the carbonyl group, its location must be indicated by a number between the root and suffix

  3. If there are side groups on the main chain, they are named and numbered in the same way as for hydrocarbons

  4. The parent chain must contain the carbonyl group and is numbered from the end closest to the carbonyl group
• Drawing ketones


  1. Add the double bonded oxygen on the carbon indicated in the name

  2. Fill in the rest of the bonds with hydrogens, giving each carbon a total of 4 bonds

  
• Practice Questions


  • p. 52 #96-98, 100, 101, 102, 104, 105abc
  • p. 56 #106-115
  • p. 61 #116-125
  • p. 65 #126, 127, 129-131
  • p. 79 #159-169