1 / 42

Hydrocarbon Derivatives:

Halocarbons, Alcohols, & Ethers. Hydrocarbon Derivatives:. Hydrocarbons. Contain only carbon & hydrogen But carbon can also form strong covalent bonds with other elements such as: O, N, F, Cl, Br, I, S, & P. Functional Group.

Download Presentation

Hydrocarbon Derivatives:

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript


  1. Halocarbons, Alcohols, & Ethers Hydrocarbon Derivatives:

  2. Hydrocarbons • Contain only carbon & hydrogen • But carbon can also form strong covalent bonds with other elements such as: O, N, F, Cl, Br, I, S, & P

  3. Functional Group • functional group: atom or group atoms in organic molecule that always behaves the same way • Adding functional group changes chemical & physical properties in specific ways • depends on type functional group added

  4. Intermolecular Forces • Determine Boiling Point & Solubility • Van der Waals or dispersion: weakest • nonpolar molecules • Dipole-dipole: intermediate strength • molecule has atoms with different electronegativities • atoms not arranged symmetrically • Hydrogen bonding: strongest • molecules contain H bonded to F, O, or N

  5. Functional Groups • Halocarbons • Alcohols • Ether • Aldehydes • Ketones • Carboxylic Acid • Ester • Amines • Amide • Amino Acid

  6. Organic Halides • One (or more) hydrogen atoms in alkane is replaced with halogen atom (F, Cl, Br, or I) • No longer hydrocarbons! • called halocarbons, alkyl halides or organic halides

  7. Naming Halides • Figure out backbone name • prefixes specify substituent: fluoro, chloro, bromo, iodo • use di, tri, tetra (if more than one same thing) • Give location(s) of halogen(s) • tell # C attached to in backbone

  8.        C3H7F CH3Cl CH3CHFCH3 H H H H–C–C–C–H HFH H H–C–Cl H 2-fluoropropane chloromethane

  9. Naming Halides CH3CCl2CHClCH3 HCl H H H –C – C – C – C– H HCl Cl H 2,2,3-trichlorobutane C4H7Cl3

  10. Ranking Halogens • If more than 1 kind halogen atom present – name them alphabetically • # C’s so lowest number goes to halogen alphabetically first

  11. 2-chloro-4-fluoro-3-iodobutane Different Halogens 4 3 2 1 Chlorine is 1st alphabetically, so it determines numbering:

  12. Br CH3CH2CHCHCH3 I 3-bromo 2-iodo pentane F Cl HCCH F Cl 1,1-dichloro-2,2-difluoroethane Name:

  13. Stronger intermolecular forces Properties of Halocarbons • alkane & alkyl halide of similar size & shape: • alkyl halide has higher bp & higher density Why? • CH4: bp = -162C density = 0.423 g/ml • CH3Cl: bp = -24C density = 0.911 g/ml

  14. Boiling Point (C) Density (g/ml) CH3CH2CH2CH2CH3 pentane 36 0.626 CH3CH2CH2CH2CH2F 1-fluoropentane 63 0.791 Inc Inc CH3CH2CH2CH2CH2Cl 1-chloropentane 108 0.882 CH3CH2CH2CH2CH2Br 1-bromopentane 130 1.218 CH3CH2CH2CH2CH2I 1-iodopentane 155 1.516

  15. Uses of Alkyl Halides • Cleaners & solvents • Examples: • Teflon & PVC’s • Refrigerants (used to be chlorofluorocarbons- now hydrofluorocarbons)

  16. Halogen Derivatives • CH3Cl = local anesthetic • CHCl3 = solvent, general anesthetic • CHI3 = antiseptic • CCl4 = dry cleaning solvent • CF2Cl2 = refrigerant • Fluorocarbons = teflon, lubricants, synthetic blood • Chlorofluorocarbons = aerosol propellants, refrigerants

  17. Table R • General Formula halocarbons: R-X • R represents entire hydrocarbon part of molecule • X represents halogen (F, Cl, Br, or I)

  18. OH H HCOH H H HCH H     Alcohols • OH group replaces H in hydrocarbon • OH group called: hydroxyl group

  19. Alcohols are nonelectrolytes! • hydroxyl group = hydroxide ion of inorganic bases - does not form ions in water! • The hydroxyl group is polar • alcohols soluble in water

  20. Naming AlcohOLs • Based on alkane name • Name parent chain • Drop the –e and add –ol • If parent chain has 3+ C’s, # which C OH group(s) attached to

  21. H H H H HCCCCH OHH H H Note: Never more than one OH group per C Naming H H H H HCCCCH HOHH H 1-Butanol bp = 100C 2-Butanol Bp = 115C

  22. More than 1 hydroxyl group • Prefixes di-, tri-, tetra- used before ol ending tell # of hydroxyl groups

  23. Classifying Alcohols • By # of hydroxyl groups • Monohydroxy: 1 hydroxyl group • Dihydroxy: 2 OH groups • Trihydroxy: 3 OH groups • By position of each hydroxyl group on main carbon chain

  24. Monohydroxy Alcohols • Primary: hydroxyl group attached to end C of chain or branch • Secondary: hydroxyl group attached to C in chain bonded to 2 other C’s • Tertiary: hydroxyl group attached to C at a branch point (C bonded to 3 other C’s)

  25. H H H H H-C-C-C-C-O-H H H H H 1-butanol (primary) H H H H H-C-C-C-C-H H HO H H 2-butanol (secondary)

  26. H H-C-H H H H-C-C-C-H HOH H 2-methyl 2-propanol (Tertiary)

  27. H H H-C─C-H O O H H H H H H-C─C─C-H O O O H H H Dihydroxy Trihydroxy

  28. Properties of Alcohols • Contain: H bonded to O atom • Hydrogen Bonding • Alcohols have higher bp than corresponding alkane • ‘Like dissolves Like’ • Alcohols tend to be very soluble in water

  29. R - O R - H O + H +

  30. Correct response = D Which compound has the highest boiling point? • CH4 • C2H6 • C3H8 • C3H7OH

  31. Table R • General Formula Alcohols: ROH • R represents entire hydrocarbon part of molecule • OH is hydroxyl group

  32. Ethers • General formula ROR • where R may or may not be same as R • R and R are hydrocarbon branches • O is oxygen bridge • Ethers are not linear • they are bent, like water

  33. Properties of Ethers • Pure ether: no hydrogen bonding • weak dipole-dipole interactions • bent, like H2O • Ethyl ether once used as anesthesia

  34. Properties of Ethers • Compared to alkanes (same # C’s): • Higher bp’s than similar alkanes • More soluble in water than alkanes • Compared to alcohols (same # C’s): • Lower bp’s than similar alcohols • Much less soluble in water than alcohols

  35. Naming Ethers • If both hydrocarbon branches are identical: • name the branch (once) & add the word ether • If 2 branches are different: • list them in alphabetical order followed by the word ether

  36. Methyl Ether Propyl Ether H H HCOCH H H H H H H H H HCCCOCCCH H H H H H H

  37. Methylpropyl Ether H H H H HCOCCCH H H H H

More Related