Tang 02 alcohols, aldehydes, ketones 2

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  • 1. ALCOHOLS, ALDEHYDES, & KETONES
  • 2. ALCOHOLS, ALDEHYDES, & KETONES
  • 3. Alcohols (-OH)
    • IUPAC naming system
    • A C-chain containing an –OH ( alcohol / hydroxyl ) functional group will have an
    • – ol ending that replaces the “e” of an
    • – ane, – ene or –yne ending.
    • CH 3 OH
    • CH 3 CH 2 OH
    • CH 3 CH 2 CH 2 OH
    methanol ethanol 1-propanol ALCOHOLS
  • 4. Example #1
    • CH 3 CHOHCH 3
    • CH 2 =CHCH 2 CH 2 OH
    CH 3 OH HO 2-propanol or isopropanol but-3-en-1-ol 4-methylcyclohexa-1,2-diol ALCOHOLS
  • 5. Example #2
    • Draw the following molecules:
    • 3-ethyl-1-hexanol
    • 2,3,3,-trimethyl-1-pentanol
    • 3-ethyl-2,4-dimethyl-5-propyl-6-octyne-1,2,5-triol
    ALCOHOLS OH OH OH OH OH
  • 6. Example #2
    • 1,5-heptadien-3-ol
    • 1,2,3-cyclopentanetriol
    ALCOHOLS OH OH OH OH
  • 7. Alcohol Nomenclature
    • Common naming system
    • Although the IUPAC system is preferred, many compounds are still referred by their “ common ” names.
    • methanol
    • ethanol
    • isopropanol
    methyl alcohol ethyl alcohol isopropyl alcohol ALCOHOLS
  • 8. Properties of Alcohols
    • Alcohols typically have higher boiling points than their hydrocarbon counterparts. Why?
    • The shorter the carbon chain of an alcohol, the more water soluble the compound. Why?
    Alcohols have hydroxyl groups (OH) which can form hydrogen bonds with one another. Hydrogen bonds are stronger than the London dispersion forces that form between their hydrocarbon counterparts. Thus more energy is required to break these stronger intermolecular bonds. Water bonds to other water molecules via hydrogen bonds. They would preferentially form hydrogen bonds with each other over weaker Van der Waals forces with long carbon chains. ALCOHOLS
  • 9. Homework
    • Textbook
    • p41 #1-3
    • p42 #4-5
    ALCOHOLS
  • 10. Aldehydes and Ketones
    • Both of these groups contain a C=O ( carbonyl group ). The location of this group determines whether a compound is an aldehyde or a ketone.
    aldehyde ketone ALDEHYDES
  • 11. Aldehyde Nomenclature
    • The aldehyde group must be included in the main C-chain to be named and labeled as carbon #1.
    • IUPAC naming system
    • The “e” of –ane, –ene, or –yne will be replaced with an “ –al ” ending.
    ALDEHYDES
  • 12. Other Nomenclature Prefixes ALDEHYDES # of carbons IUPAC Common System 1 meth- form- 2 eth- acet- 3 prop- proprion- 4 but- butyr-
  • 13. Aldehyde Nomenclature
    • Common naming system
    • methanal
    • ethanal
    • propanal
    • butanal
    formaldehyde acetaldehyde proprionaldehyde butyraldehyde ALDEHYDES
  • 14. Example #3
    • Redraw and name the following compound:
    • CH 2 =CHCH 2 CHO
    3-butenal ALDEHYDES H O
  • 15. Example #4
    • Draw and name all aldehydes with the formula C 5 H 10 O.
    pentanal 3-methylbutanal 2-methylbutanal 2,2-dimethylpropanal ALDEHYDES H O H O H O H O
  • 16. Ketone Nomenclature
    • A compound is a ketone when the carbonyl group is not found on the end of a carbon chain. When naming, the main chain must contain this group.
    • IUPAC naming system
    • The “e” of the –ane, –ene or –yne ending will be replaced with an “ –one ” ending.
    KETONES
  • 17. Example #5
    • Redraw and name the following compound:
    • (CH 3 ) 2 CHCH 2 COC(CH 3 ) 3
    2,2,5-trimethyl-3-hexanone KETONES O
  • 18. Example #6
    • Draw the following compounds:
    • 2-methyl-1,4-cyclohexanedione
    • 4-ethyl-2-methylcyclopentanone
    KETONES O O O
  • 19. Example #6
    • all ketones with the formula C 5 H 10 O
    2-pentanone 3-pentanone 3-methyl-2-butanone KETONES O O O
  • 20. Example #7
    • What is the chemical structure of the smallest aldehyde?
    • What is the chemical structure of the smallest ketone?
    KETONES O H H O
  • 21. Properties of Aldehydes and Ketones
    • Aldehydes and ketones have lower boiling points than their corresponding alcohols. Why?
    • How do these compounds compare in water solubility compared to alcohols and to hydrocarbon chains?
    They do not have OH groups so they do not participate in hydrogen-bonding. They can form weaker dipole-dipole interactions. They are less soluble because they do not form hydrogen bonds with water. KETONES
  • 22. Homework
    • p51 #1-3
    • p52 #4bc - 5
    KETONES