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REACTIONS OF ORGANIC COMPOUNDS

REACTIONS OF ORGANIC COMPOUNDS. Textbook: Chapter 2. Cancer and TAXOL. Read page 56 of your text and answer the following: What is TAXOL? Where is it found? What was so exciting about the discovery of the compound in the European yew?

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REACTIONS OF ORGANIC COMPOUNDS

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  1. REACTIONS OF ORGANIC COMPOUNDS Textbook: Chapter 2

  2. Cancer and TAXOL Read page 56 of your text and answer the following: • What is TAXOL? Where is it found? • What was so exciting about the discovery of the compound in the European yew? • Explain why the study of organic chemistry is really the study of functional groups.

  3. The Main Types of Organic Reactions • Addition • Substitution • Elimination • Oxidation • Reduction • Condensation • Hydrolysis

  4. Addition • Atoms are added to a double or triple bond • (decrease in multiple bonds) • Two compounds usually react to form one major product.

  5. Substitution • Hydrogen atom or a functional group is replaced by a different functional group. • Two compounds usually react to form two different products.

  6. Elimination • Atoms removed from a molecule to form a double bond. • Reverse of addition. • More multiple bonds • One reactant usually breaks up to form two products.

  7. Oxidation • In organic chemistry, oxidation is a reaction in which a carbon atom forms more bonds to oxygen or less bonds to hydrogen. • (Increase C-O or decrease C-H).

  8. Reduction • Carbon atoms forms fewer bonds to oxygen, O, or more bonds to hydrogen, H. • Less C-O or C-C bond. (ex// C=O to C-O). • Opposite of oxidation.

  9. Condensation • Two organic molecules combine to form a single organic molecule. • Water is usually produced.

  10. Hyrolysis • Reverse of condensation • Water is added to a bond, splitting the organic molecule into two.

  11. Classifying Reactions • Complete the following table. This is to help you identify different kinds of reactions easier!

  12. Identifying Reactions • PP pg. 63

  13. 2.1 Homework Page 63, # 1 b,c. #2 b, c. #3 b. #4 b. SR, page 64, #1 - 5

  14. 2.2 Reactions of Functional Groups Alkenes and Alkynes have ____________ or ________ bonds. Multiple bonds are more ____________ than single bonds. • Alkenes and Alkynes undergo addition reactions involving: • H and OH (from water) • H and X (from XH) where X=Cl, Br, or I. • X and X (from X2) where X=Cl, Br, or I. • H and H (from H2).

  15. Symmetry of Reactants • The product of an addition reaction depends on the symmetry of the reactants. • Symmetrical alkene: identical groups on either side of double bond. E.g. Ethene: • Asymmetrical. E.g. Propene.

  16. Added molecules can also be symmetrical/assymetrical. • Symmetrical: E.g. Chlorine. • Asymetrical: E.g. Water.

  17. What do you notice about these reactions? _________________________________________________________________________________________________________________

  18. What do you notice about this reaction? _________________________________________________________________________________________________________________

  19. Markovnikov’s Rule • Used when the products are two isomers. • Determines which isomer will be most prominent (only a small amount of other isomer will be produced). • MARKOVNIKOV’s RULE: the halogen atom or OH group in an addition reaction is usually added to the carbon bonded to the most carbon atoms.

  20. Determining the Product of a Reaction PP, page 67.

  21. Addition to Alkynes • Since alkynes have triple bonds, _________ addition reactions can take place in a row. • If one mole of a reactant, such as HCl, Br2, or H2O is added to one mole of an alkyne, the result is a substituted alkene. • If two moles of the reactant are added to one mole of an alkyne, a second addition reaction takes place, producing an alkane.

  22. Markovnikov’s Rule and Alkynes Asymmetrical alkynes follow M.’s rule. when an asymmetrical molecule is added to the triple bond. Note: the halogen is bonded to the carbon around the triple bond that is bonded to the most carbons. The hydrogen is bonded to the carbon around the triple bond that has the most hydrogens. THE RICH GET RICHER!

  23. Reactions of Aromatic Compounds • Benzene’s stable ring does not usually accept the addition of other atoms. • Aromatic compounds undergo substitution. • Addition reaction does not occur because the product of this reaction would be less stable than benzene.

  24. Reactions of Alcohols • Substitution Reactions of Alcohols • When a Halogen acid, such as HCl, HBr, or HI, reacts with an alcohol, the halogen atom is substituted for the OH group of alcohol. • An alcohol is a product when an alkyl halide reacts with OH- in a basic solution.

  25. Elimination Reactions of Alcohols • When an alcohol is heated in the presence of a strong acid and dehydrating agent, H2SO4, elimination reaction occurs.

  26. Oxidation of Alcohols • In the presence of an oxidizing agent, an alcohol is oxidized to form an aldehyde or ketone. • A primary alcohol is oxidized to an aldehyde. If the aldehyde is oxidized further, it becomes carboxylic acid. • A secondary alcohol is oxidized to a ketone. (Can a further oxidation occur?) • A tertiary alcohol cannot be oxidized.

  27. PP pg. 73 #9-13.

  28. Oxidation of Aldehydes and Ketones • Aldehydes and ketones react differently with oxidizing and reducing agents. Oxidation of Aldehydes In the presence of oxidizing agent, aldehydes will become carboxylic acids. Oxidation of Ketone Like tertiary alcohols, ketones do not have a Hydrogen atom available to be removed. C-C bonds are too strong to be broken by an oxidizing agent.

  29. Reduction of Aldehydes and Ketones • Aldehydes are reduced to produce primary alcohols. • Ketones are reduced to produce secondary alcohols.

  30. Reactions of Carboxylic Acids • Like other acids, carboxylic acid reacts with a base to produce a salt and water. • A carboxylic acid reacts with an alcohol to produce an ester. A strong acid (e.g. Sulfuric acid) catalyzes the reaction. • ESTERIFICATION REACTION!  SPECIAL CONDENSATION REACTION.

  31. Reactions of Esters and Amides • Both undergo hydrolysis reactions. • Hydrolysis of an ester produces a carboxylic acid and an alcohol. • The hydrolysis of an amide produces a carboxylic acid and an amine. • Hydrolysis can be acidic or basic hydrolysis. • In acidic: org. Mol. Reacts with water in the presence of an acid. • In basic: org. Mol. Reacts with OH- ion, from base or water in the presence of a base. SOAP IS MADE BY THE BASIC HYDROLYSIS OF ESTER ONDS IN OILS OR FATS.

  32. Concept Organizer

  33. PPs, pg. 78, #14-17 SR, pg. 79, #1-8.

  34. 2.3 – Molecules on a Larger Scale: Polymers and Biomolecules • For the most part, we have seen small organic molecules so far. • Many of the organic molecules that are used industrially, such are plastics, are large organic molecules. POLYMER: very long molecule made by linking together many smaller ‘building blocks.’ MONOMER: the ‘building blocks.’ (PAPER CLIPS)

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