Hydrocarbon Derivatives

1. Hydrocarbon Derivatives Alcohols Haloalkanes Aldehydes Ketones Carboxylic Acids Esters Ethers Amines Amides

2. Hydrocarbon Derivatives • These are organic compounds that are based on hydrocarbons with the addition of specific functional groups • A functional group is a reactive group of atoms (eg. –OH)

3. Due to the reactivity of the functional groups, we can determine the physical and chemical properties of compounds • We also classify compounds based on these groups • We will now explore six groups of hydrocarbon derivatives

4. Alcohols

5. Alcohols • An organic compound containing the hydroxyl, –OH, functional group • Have the general formula of R—OH • The “R” represents the alkyl group • Example: CH3—CH2—OH

6. Naming Rules • Locate the longest carbon chain (must contain the carbon attached to the –OH group.) Name the parent alkane • The suffix is –ol; indicate the position of the –OH group in front of the suffix • More than one –OH group; use di, tri, tetra and keep entire root name • Number the chain so that the –OH group has the lowest number • Add a position number before the name of the root to indicate the position of the –OH group • Name and number any branches (as you would for alkanes) • Put it all together: branches + root

7. Try it! • Name this alcohol: CH3—CH2—CH2—OH CH3—CH—CH2—CH2—CH3 | OH

8. One more... • Name this alcohol and state whether it is primary, secondary or tertiary. CH3—CH—CH2—CH2—CH3 | OH

9. Draw: 3,4-dimethylhexan-2-ol Butane-1,3-diol

10. Three classes of Alcohols • Primary Alcohol (1°) – the OH group is bonded to a carbon that is only bonded to one other carbon • Secondary Alcohol (2°)– the OH group is bonded to a carbon that is bonded to two other carbon atoms • Tertiary Alcohol (3°)– the OH group is bonded to a carbon that is bonded to three other carbon atoms

11. Physical properties of alcohols • Polar or non-polar? • Boiling points? Intermolecular forces?

12. Haloalkanes • HCs with at least one halogen atom • Basic structure R-X, where R is the root and X can be F, Cl, Br, I • Often result of substitution reactions • Eg. Chloroform, CFCs (refrigerants & propellants)

13. Naming haloalkanes • Identify the root – longest continuous chain • Identify the suffix – which family • Type of halogen (F-fluoro, Cl-chloro, Br-bromo, I-iodo); more than one – di, tri, etc • Halogen gets the lowest number • Then look for alkyl groups • .Halogen substituent groups and alkyl side groups are arranged alphabetically

14. Try these… • CH3-CH2-CH2-Cl • CH2=CH-CH2-Br • Try #85-95 on page 49

15. Physical properties • polarity/solubility in water? • Boiling points?

16. Aldehydes

17. Aldehyde • Contain a formyl group, which is a carbonyl functional group >C=O with a H bonded to the C atom Only one possible position – always C#1 • Have characteristic scents and tastes • Example – Cinnamon or Formaldehyde, vanillin, cilantro

18. Naming Aldehydes • As with other naming (ID root) • The carbonyl group will always be on a terminal carbon, thus there is no need to give a position number • Simply name the carbon chain; drop the –e from the end and add –al; give the C=O position 1 • Add branches (if any) as you have for all others!

19. Try Some O HC—CH2—CH2—CH3 CH3—CH2—CH—CH Try page 52: #96-105 || O || | CH2—CH3

20. Physical properties of aldehydes • Polarity? • Boiling points? Compared to alcohols?

21. Ketones

22. Ketones • Contain the carbonyl group C=O • Has an alkyl group on either side of the C=O • General formula R-CO-R`

23. Naming Ketones • Find the longest carbon chain containing C=O • Number the chain so that C=O has lowest number • Drop the final –e from the alkane name and add –one • Name and add branches as you would for alkanes

24. Try These O CH3—CH2—CH2—C—CH3 CH3—CH—C—CH2—CH2—CH3 | CH3 || O ||

25. Carboxylic Acids

26. Carboxylic Acids O • Contain a carboxyl group —C—OH • General formula of R—COOH • Polar molecules • Soluble in water • Have high MP and BP ||

27. Naming Carboxylic Acids • Name the parent alkane; drop the –e at the end of the alkane name and add –oic acid • Carboxyl group is always given position one (no need to state this!) • Name any branches as we do for alkanes

28. Try some O CH3—C—OH CH3—CH—CH2—C—OH | CH3 || O ||

29. esters

30. Esters • Derivatives of carboxylic acids • Contains the functional group —C—O— • General formula RCOOR` • Example: CH3—CH2—C—O—CH3 O || O ||

31. Naming Esters • Choose the main part of the ester, containing the C=O group. Name this as the parent acid. • Replace the –oic acid with –oate • Name the second part of the ester as an alkyl group • Put them together – alkyl group + parent acid

32. CH3—CH2—C—O—CH3 We would name this methyl propanoate O || Alkyl Group Parent acid

33. Try One CH3—CH2—CH2—CH2—C—O—CH2—CH3 O ||

34. Ether

35. Ethers • An organic compound that has two alkyl groups joined by an oxygen atom • Has the general formula of R—O—R` • R and R` indicate two alkyl groups • The can be the same or different • Example: CH3—CH2—O—CH3

36. How do we get to this? • You can think of alcohols and ethers as derivatives of water! H—O—H Water R—O—H Alcohol R—O—R` Ether

37. Rules for naming Common Names • List the alkyl groups that are attached to the oxygen atom, in order of increasing length. • Place the suffix –ether at the end of the name No numbers are needed to show the location of the oxygen atom!

38. Try it! Name these ethers CH3—CH2—O—CH2—CH2 CH3—CH2—CH2—CH2—O—CH2—CH3