Recommended
More Related Content
What's hot
What's hot (20)
Similar to Chapter 12 wiley
Similar to Chapter 12 wiley (20)
Recently uploaded
Recently uploaded (20)
Chapter 12 wiley
- 1. Chapter 12 Review HELLO EVERYONE AND WELCOME TO ORGANIC CHEMISTRY THE ONLY CLASS THAT MAKES TALKING ABOUT ALCOHOL BORING
- 2. Review of Chapter 7: Sn1 •Sn1 • Involves carbocation intermediate • Racemic mixture as product • Weak nu: • Rate increases with increasing number of substituents • Mechanism
- 3. Review of Ch.7: Sn2 •Inversion of stereochemistry •1 step •Need a strong nucleophile •Less R groups the better •Mechanism
- 4. Review of Ch.7: E1 •Really only used in one reaction in this chapter • Weak base • Carbocation intermediate= rate-limiting step • Mechanism
- 5. Review of Ch.7: E2 •Strong base •Concerted reaction •ZAITSEV AND HOFFMAN •Mechanism
- 7. Whats what
- 8. Naming Alcohol •Take off “–e” ending an replace it with “–ol” •Prior to suffix –ol include the position of the hydroxy •Just like in life, alcohol takes top priority, for now •If on a ring, DO NOT NUMBER THE ALCOHOL •2 alcohols? Use suffix -diol
- 9. Practice
- 10. Physical properties •For solubility questions, use 5 carbon rule •As R groups increase, ability to H bond decreases •Alcohols have really strong hydrogen bonds •Ethers and epoxides have dipole-dipole interaction
- 11. practice
- 12. Chapter 9 In A Nutshell •The first step is to make OH a good leaving group •The next step is generally going to be Sn1, Sn2, E1, E2 •The key to this chapter is going to be figuring out what the second step is •If you don’t know, use rules from Chapters 7 This Photo by Unknown Author is licensed under CC BY- SA-NC
- 13. Alcohol Preparation Reactions •How? • Reduce a carbonyl (Use LiAlH4 or Grignard) -Mechanism • Substitution reaction • Addition reaction
- 15. Reduction of Esters •Mechanism •Enantiomers are formed •CANNOT be done with NABH4 •If you use a Grignard then you get a tertiary alcohol
- 16. Reduction of aldehydes/ketones •This is similar to the last mech but shorter •Forms enantiomers •Can be done NaBH4 as well •Grigrnard + ketone tertiary alcohol •Grignard + aldehyde secondary alcohol
- 17. Alcohol reactions •What I can do? •Oxidize •Cant really reduce anymore •Substitution •Elimination
- 19. Dehydration Reactions •H2SO4 •This Likes to do E1 •Mech for the second one
- 20. practice
- 21. Dehydration with Phosphoryl Chloride •POCl3 in pyridine •POCl3 makes OH a good leaving group •Pyridine acts as a base so we can eliminate •I THINK THAT THIS IS FROM MY OTHER ORGO CLASS
- 22. Mechanism for POCL3 (GHOST OF ORGO PAST)
- 23. Conversion of Alcohol To Alkyl Halide •HX where X=Br •HCl with ZnCl2 •Cl needs the Lewis acid, ZnCl2, because it is a weaker Nu: •SOCl2 (Sulfur is in same family as oxygen) • Mechanism •PBr3 (phosphorus is in same family as Nitrogen) • Mechanism
- 25. Mechanism (PBr3)
- 26. Mechanism (HX) •The first step is protonation of OH to form water •Second step is Sn1 or Sn2 •For HCl, there is a intermediate involving ZnCl2, but don’t worry about it.
- 27. practice
- 28. Practice
- 29. Tosylates •Use alcohol and TsCl • This forms a good leaving group •Mechanism ( the second step can be anything)
- 30. Practice I also like 9.27
- 31. Oxidation of alcohols •Primary alcohol aldehyde via PCC •Primary alcohol carboxylic acid via Na2Cr2O7 •Secondary alcohol ketone vai PCC or Na2Cr2O7 •DO NOT WORRY ABOUT THE MECHANISM