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Chapter 4 Alcohols and Alkyl Halides

Chapter 4 Alcohols and Alkyl Halides. Overview of Chapter. This chapter introduces chemical reactions and their mechanisms by focusing on two reactions that yield alkyl halides. (1) alcohol + hydrogen halide ROH + HX  RX + H 2 O (2) alkane + halogen

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Chapter 4 Alcohols and Alkyl Halides

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  1. Chapter 4Alcohols and Alkyl Halides

  2. Overview of Chapter This chapter introduces chemical reactions and their mechanisms by focusing on two reactionsthat yield alkyl halides. (1) alcohol + hydrogen halide ROH + HX  RX + H2O (2) alkane + halogen RH + X2 RX + HX Both are substitution reactions.

  3. 4.1Functional Groups

  4. Functional Group A structural unit in a molecule responsible for itscharacteristic behavior under a particular set ofreaction conditions.

  5. Families of Organic Compoundsand their Functional Groups Alcohol ROH Alkyl halide RX (X = F, Cl, Br, I) Amine primary amine: RNH2 secondary amine: R2NH tertiary amine: R3N

  6. C C O Families of Organic Compoundsand their Functional Groups Ether ROR' Nitrile RCN Nitroalkane RNO2 Sulfide RSR' Thiol RSH Epoxide

  7. O O C C Many Classes of Organic Compounds Contain a Carbonyl Group R Carbonyl group Acyl group

  8. O O C C Many Classes of Organic Compounds Contain a Carbonyl Group H R Carbonyl group Aldehyde

  9. O O C C Many Classes of Organic Compounds Contain a Carbonyl Group R' R Carbonyl group Ketone

  10. O O C C Many Classes of Organic Compounds Contain a Carbonyl Group OH R Carbonyl group Carboxylic acid

  11. O O C C Many Classes of Organic Compounds Contain a Carbonyl Group OR' R Ester Carbonyl group

  12. O O C C Many Classes of Organic Compounds Contain a Carbonyl Group NH2 R Amide Carbonyl group

  13. 4.2IUPAC Nomenclatureof Alkyl Halides

  14. IUPAC Nomenclature There are several kinds of IUPAC nomenclature. The two that are most widely used are:functional class nomenclaturesubstitutive nomenclature Both types can be applied to alcohols andalkyl halides.

  15. CH3CH2CHCH2CH2CH3 H I Br Functional Class Nomenclature of Alkyl Halides Name the alkyl group and the halogen asseparate words (alkyl + halide). CH3F CH3CH2CH2CH2CH2Cl

  16. CH3CH2CHCH2CH2CH3 H I Br Functional Class Nomenclature of Alkyl Halides Name the alkyl group and the halogen asseparate words (alkyl + halide). CH3F CH3CH2CH2CH2CH2Cl Methyl fluoride Pentyl chloride 1-Ethylhexyl bromide Cyclohexyl iodide

  17. CH3CHCH2CH2CH3 Br CH3CH2CHCH2CH3 I Substitutive Nomenclature of Alkyl Halides Name as halo-substituted alkanes. Number the longest chain containing thehalogen in the direction that gives the lowestnumber to the substituted carbon. CH3CH2CH2CH2CH2F

  18. CH3CHCH2CH2CH3 Br CH3CH2CHCH2CH3 I Substitutive Nomenclature of Alkyl Halides Name as halo-substituted alkanes. Number the longest chain containing thehalogen in the direction that gives the lowestnumber to the substituted carbon. CH3CH2CH2CH2CH2F 1-Fluoropentane 2-Bromopentane 3-Iodopentane

  19. Cl CH3 CH3 Cl Substitutive Nomenclature of Alkyl Halides Halogen and alkyl groupsare of equal rank when it comes to numberingthe chain. Number the chain in thedirection that gives the lowest number to thegroup (halogen or alkyl)that appears first.

  20. Cl CH3 CH3 Cl Substitutive Nomenclature of Alkyl Halides 5-Chloro-2-methylheptane 2-Chloro-5-methylheptane

  21. 4.3IUPAC Nomenclatureof Alcohols

  22. CH3 CH3CCH2CH2CH3 OH CH3CHCH2CH2CH2CH3 OH Functional Class Nomenclature of Alcohols Name the alkyl group and add "alcohol" as aseparate word. CH3CH2OH

  23. CH3 CH3CCH2CH2CH3 OH CH3CHCH2CH2CH2CH3 OH Functional Class Nomenclature of Alcohols Name the alkyl group and add "alcohol" as aseparate word. CH3CH2OH Ethyl alcohol 1,1-Dimethylbutylalcohol 1-Methylpentyl alcohol

  24. CH3 CH3CCH2CH2CH3 OH CH3CHCH2CH2CH2CH3 OH Substitutive Nomenclature of Alcohols Name as "alkanols." Replace -e ending of alkanename with -ol. Number chain in direction that gives lowest numberto the carbon that bears the —OH group. CH3CH2OH

  25. CH3 CH3CCH2CH2CH3 OH CH3CHCH2CH2CH2CH3 OH Substitutive Nomenclature of Alcohols Name as "alkanols." Replace -e ending of alkanename with -ol. Number chain in direction that gives lowest numberto the carbon that bears the —OH group. CH3CH2OH Ethanol 2-Methyl-2-pentanol or 2-Methylpentan-2-ol 2-Hexanol or Hexan-2-ol

  26. OH CH3 CH3 OH Substitutive Nomenclature of Alcohols Hydroxyl groups outrank alkyl groups when it comes to numberingthe chain. Number the chain in thedirection that gives the lowest number to thecarbon that bears theOH group

  27. OH CH3 CH3 OH Substitutive Nomenclature of Alcohols 6-Methyl-3-heptanol 5-Methyl-2-heptanol

  28. 4.4Classes of Alcoholsand Alkyl Halides

  29. Classification Alcohols and alkyl halides are classified asprimary secondary tertiaryaccording to their "degree of substitution." Degree of substitution is determined by countingthe number of carbon atoms directly attached tothe carbon that bears the halogen or hydroxyl group.

  30. CH3 CH3CHCH2CH2CH3 CH3CCH2CH2CH3 Br OH Classification H CH3CH2CH2CH2CH2F OH primary alkyl halide secondary alcohol secondary alkyl halide tertiary alcohol

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