2091 10690 CHEM 0310 ORGANIC CHEMISTRY 1 2091 10690 COURSE DOCUMENTS CHAPTER 8 ALCOHOLS SYNTHETIC STRATEGIES Chapter 8 Alcohols Synthetic Strategies Last Updated on 8 November 2008 Textbook Typos Chapter 8 Page 302 Exercise 8 10 c The answer on page A 11 to this in text exercise incorrectly shows an di alcohol it should show an di aldehyde identified by ES Chapter 8 Page 313 the first retrosynthetic chemical equation At the top of the page under The Retrosynthetic Anaylysis of 3 Hexanol Synthesis 3 hexanol is transformed into propylmagnesium bromide and propanal Rather than being written as CH3CH2CH2MgBr the propylmagnesium bromide fragment is incorrectly shown as CH3CH2CH2M2Br identified by SW Chapter 8 Page 313 the first retrosynthetic chemical equation In the middle of the page the authors have a header suggesting a second way of retrosynthetic disconnection by breaking the C4 C5 They should have labeled it the C2 C3 bond of 3 hexanol identified by ES Chapter 8 Page 315 Exercise 8 17 the retro synthetic equation at the bottom of the page following the first retrosynthetic arrow the alcohol is shown having 9 carbons rather than the 7 carbons in the target i e the seven carbons in the structure before the retrosynthetic arrow This error is propagate in the remainder of this equation identified by MD Chapter 8 Page 318 Chapter Integration Problem 8 19 the master retro synthetic chart pathway C of breaking the starting material into two fragments yields an organometallic reagent with 3 carbons and a ketone with 11 carbons a total of 14 carbons While the starting material itself contains only 13 carbons The organometallic reagent in pathway C should only contain 2 carbons identified by MD Chapter 8 Page 325 4th item in the Important Concepts section The organometallic compound shows that the metal has a partial positive charge delta but fails to correctly show that the carbon has a partial negative charge delta It only shows the delta above the carbon with no minus sign identified by JT If you spot any that have not already been identified for this chapter use the appropriate Discussion Board forum under the Communication tab to identify it and to receive extra credit points Introduction This chapter signals a subtle shift in the strategy of Orgo So far we have concentrated on a small number of toics but developed a high degree of understanding of subtantial and new topics Beginning with this chapter we will shift a bit more towards memorization and much more towards unique and artistic applications of everything we ve learned At this point in an Orgo course most students fint it useful to make one flashcard for each unique type of reaction by the end of the semester you might have 50 such cards The cards help you to study the generic reactions constaints and nuances as you continue to flesh out the detail on each flash card The artistic application is the synthesis of new molecules most of which can be made in several different ways someclearly better than the others others hardly different and still others open to debate and or personal preference Learning Objectives 1 Organic oxidation and reduction and particularly as related to alcohols 2 Organometallic reagents and their use in the synthesis of alcohols 3 Begin to develop a systematic strategy for devising sensible ways to make more valuable and usually larger organic compounds from cheaper and usually smaller ones Chapter Advice 1 This is a chapter rich in things to learn and memorize with lots and lots of practice problems Get an early start and keep a stustained effort 2 Be prepared even more than before to focus on the functional groups and their polar bonds as sits of possible reactivity EDIT VIEW 3 Complete this chapter before coming to class on Chapter Synopsis 8 1 Naming the Alcohols flip through read if interested 8 2 Structural and Physical Properties of Alcohols flip through read if interested 8 3 Alcohols as Acids and Bases important understand class discussion review section if necessary 8 4 Industrial Sources of Alcohols Carbon Monoxide and Ethene flip through read if interested 8 5 Synthesis of Alcohols by Nucleophilic Substitution important understand class discussion review section if necessary 8 6 Synthesis of Alcohols Oxidation Reduction Relation Betwen Alcohols and Carbonyl Compounds important understand class discussion review section if necessary 8 7 Organometallic Reagents Sources of Nucleophilic Carbon for Alcohol Synthesis important understand class discussion review section if necessary 8 8 Organometallic Reagents in the Synthesis of Alcohols important understand class discussion review section if necessary 8 9 Complex Alcohols An Introduction to Synthetic Strategy important understand class discussion review section if necessary Lectures Notes Unit 8 Alcohols 10 page pdf file 273 046 Kb 10 15 Lecture Notes complete with audio Wednesday 15 October 2008 complete lecture slides to accompany audio recording lecture 7 page pdf file 379 929 Kb Wednesday 15 October 2008 audio recording of lecture 23 MB wav file 22 936 Mb Note that the audio recorder does not record quiet times As a result the minute long gaps when clicker questions are being answered appear to be just a few seconds in the audio recording Electronic Resources Formation of Grignard reagent from 1 bromobutane and reaction with acetaldehyde to give 2 hexanol http bcs whfreeman com vollhardtschore5e content cat 020 ch08 08010 01 htm Reduction of pentanal with sodium borohydride http bcs whfreeman com vollhardtschore5e content cat 020 ch08 08020 02 htm Reduction of cyclobutanone with lithium aluminum hydride http bcs whfreeman com vollhardtschore5e content cat 020 ch08 08020 03 htm Exercises It is recommended that even if you do not read a section that you should work out the exercises embedded in the sections This will quickly identify if you are comfortable enough with that topic End of chapter problems required 22 25 26 27 I really like questions like 27 31 32 34 35 37 38 39 40 41 42 45 46 47 48 49 50 End of chapter problems strongly recommended 28 36 44 51 End of chapter problems useful to ensure material mastery 21 23 24 29 30 33 43 52 53 54 55 56 57 58 59 60