ch 17

• What functional group do carboxylic acids contain?

  COOH (carboxyl) group
• How are carboxylic acids abbreviated?

  As RCOOH or RCO2H
• What do esters contain that distinguishes them from carboxylic acids?

  An OR' (alkoxy) group
• How are esters abbreviated?

  As RCOOR′ or RCO2R′
• What do amides contain that distinguishes them from esters?

  A N atom bonded to the carbonyl C
• How are amides classified?

  Based on the number of C atoms bonded to N
• What is the abbreviation for a primary amide?

  RCONH2
• How many C—N bonds does a secondary amide contain?

  Two C—N bonds
• What is the abbreviation for a tertiary amide?

  RCONHR′2
• What is a cyclic ester called?

  A lactone
• What is a cyclic amide called?

  A lactam
• What do carboxylic acids, esters, and amides all contain?

  An acyl (RCO) group
• Who discovered the antibiotic properties of penicillin?

  Sir Alexander Fleming
• How does penicillin kill bacteria?

  It interferes with bacterial cell wall synthesis
• What structural feature do all penicillins contain?

  A β-lactam
• Why do many polymers end up in landfills?

  They do not degrade readily
• What does a lower recycling code indicate about a polymer?

  It is easier to recycle
• What is the recycling code for PET?

  1
• What can PET be reused to make?

  Fleece clothing and carpeting
• What happens when PET is heated with H2O and acid?

  It returns to its monomer units
• Why are slowly degrading polyesters useful for sutures?

  They hold tissue together while healing
• What are fibers like wool and silk made of?

  Proteins joined by amide linkages
• What is nylon classified as?

  A condensation polymer
• What is the most common polyester?

  Polyethylene terephthalate (PET)
• Why is PET popular for making plastic bottles?

  It is easily and cheaply made
• What is the bond angle around the carbonyl carbon?

  120 degrees
• Why is the carbonyl group polar?

  O is more electronegative than C
• What happens to the carbonyl C and O in terms of electron density?

  Carbonyl C is e− rich, O is e− poor
• What are the steps to name a carboxylic acid using the IUPAC system?

  1. Find the longest chain with COOH.
  2. Number the chain to put COOH at C1.
  3. Apply nomenclature rules.
  4. Change “-e” to “-oic acid”.
• What is the common name for acetic acid?

  Vinegar
• What is the α carbon in relation to the COOH group?

  The carbon adjacent to the COOH
• How are 1o amides named?

  By replacing “-oic acid” with “-amide”
• What is the systematic name for acetamide?

  Derived from acetic acid
• How do you name an ester using the IUPAC system?

  Change “-ic acid” to “-ate” for acyl group
• What is the first step in naming an ester?

  Name the R' group as an alkyl group
• How do you name a 2o or 3o amide?

  Name alkyl groups bonded to N with “N-”
• What is the systematic name for N-ethylformamide?

  Derived from formic acid
• What is the boiling point trend among carboxylic acids, esters, and amides?

  Carboxylic acids > 1o/2o amides > 3o amides/esters
• Why do carboxylic acids have higher boiling points than alcohols?

  More hydrogen bonding interactions possible
• Why do carboxylic acids have higher boiling points than esters?

  Esters cannot undergo hydrogen bonding