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Organic Chemistry
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  1. Organic Chemistry Part 2: Functional Groups

  2. Added to a H-C chain in place of a H at terminal C in between carbons Determine unique chemical & physical properties Examples of functional groups alkyls & halogens hydroxyl group alcohols aldehyde group carboxyl group Organic acids Ketones Ether / Esters Amine / Amide Functional Groups

  3. R - OH hydroxyl group not bases not hydroxide polyatomic ion Alcohols Functional group simply replaces one or more H in the H-C chain Hydroxyl group forms a covalent bond with a carbon atom a.k.a. non-electrolyte In bases the OH- forms an ionic bond with a + cation and will ionize a.k.a. electrolyte

  4. Monohydroxy Alcohols • Only one OH group • Primary alcohols • -OH group is bonded to a C that is bonded to 1 other C. • Secondary alcohols • -OH group is bonded to a C that is bonded to 2 other Cs • Tertiary alcohols • -OH group is bonded to a C that is bonded to 3 other Cs

  5. Structural formula, name and molecular formula? • CH3OH • CH3CH2OH • CH3CHOHCH3 • COHCH3CH3CH3

  6. Dihydroxy alcohols • Alcohols that contain 2 hydroxyl groups • CH2OHCH2OH • structural formula? • molecular formula? • name? 1, 2 - ethanediol • Common name - ethylene glycol • antifreeze

  7. Trihydroxy alcohols • 3 hydroxyl groups per molecule • CH2OHCHOHCH2OH • structural formula? • molecular formula? • Name? 1, 2, 3 - propanetriol • common name = glycerol / glycerine Alcohols with 3 OH groups end in triol

  8. Structural formula, name and molecular formula? • CH2OHCHOHCH3 • CH2OHCH2CH2COHOHCH3 • Structural formula & name? • CHBrOHCHCH3CHBrOH

  9. H C O Aldehydes • Aldehyde group is found at end of H-C chain • no number is needed to designate the aldehyde it is ALWAYS the #1 Carbon • R - CHO • aldehyde name ends in -al Ex. Formaldehyde Methanal

  10. You can add alkyl groups and halogens to an aldehyde, but remember the C=O is always the number one carbon. CH3CHCH3CH2CH2CHO Always #1

  11. Structural Formulas & Names • HCHO • CH3CH2CHO • CH3CH3CH3CCHO • CHBrBrCHO

  12. Molecular Formulaof Aldehydes • When writing the molecular formula count all C’s & H’s together and keep the functional group separate • They will all end in CHO • Ex. c.s.f. = CH3CH2CH2CHO molec. f. = C3H7CHO

  13. O C Ketones • Functional group found in middle of H-C chain • R - CO - R’ • ketone names end in - one Ex. Acetone Propanone Used as solvents

  14. Ketones Methanone Don’t exist Ethanone Propanone 2- Butanone 2- Pentanone

  15. O C Naming ketones • Designate where the functional group and side chains are located with lowest possible number given to the functional group

  16. Practice • 2-methyl-3-pentanone • 3,3-dimethyl-2-butanone • 4-methyl-3-hexanone • 5,5-dibromo-4-methyl-3-hexanone

  17. ALKYL groups O Ethers • Functional group found inside H-C chain • R - O - R’ • naming ethers • name R groups in alphabetical order • put spaces between alkyl groups and add “ether” as your ending

  18. Structural formula & name? diethyl ether a.k.a. Ether • CH3OCH3 • CH3CH2OCH2CH3 • Molecular formula? C2H5OC2H5 • CH3OCH2CH3 • Molecular formula? CH3OC2H5 • CH3CH2CH2OCH2CH2CH2CH3 • Molecular formula? C3H7OC4H9

  19. O C O H Carboxylic Acids • Functional group found at end of H-C chain • R - COOH • carboxyl group • naming • drop “e” of alkane name and add - oic acid

  20. Structural formula & name • CHOOH • methanoic acid • A.k.a. formic acid • CH3COOH • ethanoic acid • A.k.a. acetic acid • CH3CH2COOH

  21. 6,6,7-trichloro-4-methylheptanoic acid H H H Cl Cl H C H H O | | | | | | 1 H - C - C - C - C - C - C - C | | | | | | H Cl H H H H OH More complex naming • If the H-C chain contains halogen substitutions and methyl side chains number your carbons from the functional group

  22. H O C H OH H O C H O- H C H C hydronium ion 1 of 3 Properties of Carboxylic Acids • Weak ionization in water water + H2O + H3O+ ethanoic acid acetic acid acetate ion Organic acids are weak electrolytes

  23. As carboxylic acid H-C chains increase solubility decreases. #2 Properties . . . . • Solubility of R-COOH • if R = C1 - C3 • completely miscible (soluble) • if R = C4 - C5 • somewhat miscible (3.7g in 100g H2O) • if R > C5 • completely immiscible (insoluble) • fatty acids

  24. H O C H OH H C sodium hydroxide #3 Properties . . . . • Organic acids react with bases to produce salts • neutralization water + NaOH HOH + NaCH3COO sodium acetate (salt) ethanoic acid acetic acid

  25. ester Esters & Esterification • Esterification • Slow, reversible dehydration process • organic acid reacts with an alcohol • Products are an ester and water water alcohol acid

  26. Esters • Functional Group • R - COO - R’ • R groups are alkyl groups Esters have sweet fruity odors

  27. Alcohol Naming Esters 1. Name the R group bonded to the -O 2. Name the R group bonded to the = O drop the e (of the alkane name) • add -oate ACID

  28. Organic Reactions • Combustion • Burning • H-Cs in the presence of O2(g) will burn to produce CO2 and H2O X + O2 CO2 + H2O

  29. Law of Conservation of Matter • Substitution • When one or more hydrogen atoms of a H-C chain is replaced by a halogen. C2H6 + Cl2 C2H5Cl + HCl C2H6 + Cl2 C2H4Cl2 + H2

  30. Addition • Involves breaking a multiple bond • Unsaturated compounds become more saturated • Alkyne becomes an alkene • Alkene becomes an alkane C2H2 + Br2 C2H2Br2 C2H4 + Br2  C2H4Br2

  31. Polymerization • The process of bonding many small molecules (monomers) together to make a very long chain (polymer) • Water must be a product • Examples of polymers • starches • Proteins • nylon

  32. ethyl ethanoate Esterification Reaction Ethanoic acid water ethanol

  33. Structural formula & Naming • CHOOCH3 • What were the alcohol and the acid? • CH3COOCH3 • What were the alcohol and the acid? • CH3COOCH2CH3 • alcohol and acid? • CH3CH2COOCH2CH2CH2CH3 • alcohol and acid?

  34. Esterification must be done in the presence of a catalyst to make the reaction go faster Because Esterification deals with organic MOLECULES the reaction is slow

  35. Reactants Alcohol Carboxylic acid Products Ester Water Ions not involved Slow reaction needs a catalyst Reactants Acid (Org or inOrg) Base Products Salt Water Ions Fast reaction No catalyst Double Replacement Reactions Esterificationresembles Neutralization

  36. Amines • First functional group to contain Nitrogen • N can only make 3 bonds • It has a total of 5 valence electrons • 3 are unpaired

  37. methanamine Naming Amines • Drop the e from the parent chain name and add amine • You must number your carbons to show where the amine group is located

  38. butanamide Amides • Functional group containing a Nitrogen AND a carbonyl group (C=O) at the end of the chain • Carbonyl is always the #1 carbon • Drop the e from the parent chain name and add - amide

  39. Contains Na+ or K+ Looooong carboxylic acid ~ C12 - C 18 Soap • Metallic salt of a higher carboxylic acid • Most common soap • sodiumsalt of stearic acid • CH3(CH)16COONa

  40. Reactants fat or oil ester strong base NaOH KOH Products trihydroxy alcohol 1,2,3-propanetriol a.k.a. glycerol soap sodium stearate Saponification

  41. Saponification Reaction (C17H35COO)3C3H5 + 3NaOH  C3H5(OH)3 + 3C17H35COONa Sodium soap = bar soap Potassium soap = liquid

  42. Hard water • Hard water contains metallic ions ex. Ca2+ Mg2+ Fe2+ • When soap is used in hard water the stearate ion combines with these ions and forms a greasy precipitate • soap scum

  43. Charged end is hydrophillic “water loving” Non-polar end is hydrophobic “water hating” How do soaps clean? • Soaps are ionic compounds and will ionize • Na+ and CH3(CH2)16COO-

  44. H2O H2O H2O H2O H2O H2O H2O H2O Grease Greece H2O H2O H2O H2O H2O H2O H2O

  45. Animated Soap micelle

  46. Advanced Isomers • Isomers • Same molecular composition • Same number of C, H, and/or O • Different structural formula • Different chemical properties • reactivity • Different physical properties • Melting point, boiling point, vapor pressure, evaporation rate, solubility

  47. The End