CHEM353W25 MT grades and exam report were posted to D2L on Th Mar 27th. See D2L News & Examinations content folder for more IMPORTANT details about review work and grades etc.
Answer key for the scheduled MT are posted to the Exam archive. 
  
    Wk 12 
    (Apr 7-11) | 
    etext Ch 19 : Carboxylic 
      acids  
Reactions to prepare 
        carboxylic acids  &  carboxylic acid derivatives 
        Hydrolysis reactions of carboxylic acids derivatives esp. esters and amides.   
        Reactions of organometallic reagents with esters 
        Reactions of hydride reagents with esters 
        Hydride reduction of amides. 
        Reactions of nitriles with hydride and Grignard reagents 
    etext Ch 20  Enolates: why 
        all the fuss ?  Enolates of aldehydes 
          and ketones, esters.  Active 
            methylene compounds.  
            pKa of enolates 
Selected reactions of aldehyde and ketone enolates.... alkylations, the Aldol 
            condensation 
            Selected reactions of ester enolates....   the Claisen 
          condensation, Dieckmann condensation and other enolates....  overview 
          Decarboxylation 
    of beta-ketoacid 
    Corresponds to L01 content modules 16 E-H (D2L content folder will be updated as we progress)   | 
  
  
    Wk 11 
    (Mar 31-Apr 4) | 
    etext Ch 20: cont'd : Carboxylic acid derivatives : Relative 
            reactivity. 
             
            Preparations of aldehydes and ketones including oxidation 
        of alcohols 
             
        Reactions 
        of aldehydes and ketones with various nucleophilic systems : compare / contrast  mechanisms based on Nu strong 
            vs weak 
          Reactions of hydride reagents (H- as nucleophile) with aldehydes 
              and ketones to give alcohols. 
            Other reductions of aldehydes and ketones to CH2.  
           
            Reactions of organometallic reagents (C- as nucleophile) with aldehydes and ketones to give alcohols. 
          The 
          Wittig reaction (used to prepare alkenes from aldehydes and ketones). 
            Reactions of aldehydes 
                and ketones with water to form hydrates. 
        Reactions of aldehydes 
        and ketones with alcohols to form acetals and ketals : application as "protecting groups", (protecting groups for alcohols). 
etext Ch 17 :The 
  Baeyer-Villager oxidation / reaction        
Corresponds to L01 content modules 16 B-D (D2L content folder)  
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    Wk 10 
    (Mar 24-28) | 
    etext Ch 12 : How do aromatic substituents 
      influence reactivity ? (contd) 
      Substituent effects, application and implication of substituent effects. 
      etext Ch 14: Introduction to organometallic reagents - a source of nucleophilic carbon, and hydride reagents - a source of nucleophilic hydrogen. 
        Organometallic compounds : what 
          are they ? Recognising their reactivity.  Review of their reactions with epoxides.  
      etext Ch 
        17: Aldehydes and ketones : review. Typical 
          reaction mechanism : nucleophilic addition, Relative 
            reactivity. 
        etext Ch 20: Carboxylic acid derivatives : Typical 
          reaction mechanism : nucleophilic acyl substitution. Relative 
            reactivity. 
    Corresponds to content modules 14 D-E, 15, 16A (D2L content folder)   | 
  
  
    Wk 9 
    (Mar 17-21) | 
    Aromaticity Implications i.e. aromaticity impact on properties and reactions. 
      etext Ch 12 : Electrophilic 
        aromatic substitution : why this pathway ?  
        Reactions 
          of Aromatic systems.  Table 
            of reagents etc. for electrophilic aromatic substitution reactions. 
        Examples of EAr. substitution reactions. 
        Reactions of other aromatic substitutents : reductions 
          of C=O to CH2 
          Reactions involving aromatic amines ArNH2  - reduction 
              of -NO2, diazotisation ,reactions 
                of diazonium salts 
          Reactions of other aromatic 
          substitutents : reactions 
                of the benzylic position  
        etext Ch 12 : How do aromatic substituents 
      influence reactivity ?   
      Substituent effects, understanding, rationalising
      and recognising substituent effects 
    Corresponds to  content modules 14A-C (D2L content folder)  | 
  
  
    Wk 8 
    (Mar 10-14) | 
    How 
      to analyse and design an organic synthesis 
      etext Ch11 Aromatic 
        hydrocarbons and Arenes. What 
          is aromaticity ? - resonance 
            energy, aromaticity 
              criteria 
          Other aromatic systems : PAHs, heteroaromatics , other hydrocarbons and annulenes. 
          Aromaticity 
            criteria -  application to non-benzene systems (i.e. understanding aromaticity 
            of molecules like pyrrole, pyridine, furan, etc and aromatic ions). 
        Other aromatic systems : PAHs, heteroaromatics , other hydrocarbons and annulenes.     
    Corresponds to  content modules 12, 13A-C (D2L content folder)   | 
  
  
    Wk 7 
    (Mar 3-7) | 
    etext Ch 10  
      Conjugated dienes, kinetic 
        and thermodynamic control, 1,2- vs 1,4- (or direct vs conjugate) additions e.g. additions 
          of hydrogen halides (HX) 
      Conjugated dienes : direct (1,2)- and conjugate (1,4)-additions of halogens 
        (X2).  
        The Diels-Alder 
          reaction : terminology, selectivity etc. 
    Corresponds to  content modules 11B-D (D2L content folder)   | 
  
  
    Wk 6 
    (Feb 24-28) | 
    Ozonolysis 
      of alkenes and alkynes considering both oxidative and reductive work-ups. 
      Synthesis 
        of 1,2-diols via oxidation of alkenes with KMnO4 or OsO4 
      Cyclopropanation 
        reactions of alkenes 
      Study tool : make a table about the reactions (note no audio, just a table to complete from notes "review") 
  etext Ch 10 Polyenes: Terminology  - conjugation, resonance, allylic systems : reactivity 
    Corresponds to video content modules 08C,D 09-11A,B (D2L  content folder)   | 
  
  
    | (Feb 17-21) | 
    WINTER SEMESTER BREAK (no classes) | 
  
  
    Wk 5 
    (Feb 10-14) | 
    Halogenations 
          of alkenes and alkynes. 
          Halohydration of alkenes (reactions with X2 / H2O and HOX). 
      An introduction to epoxides. Preparations : epoxidation of alkenes using peracids and synthesis 
        from halohydrins via intramolecular Williamson type ether synthesis. 
      An introduction to the reactions 
        of epoxides with various nucleophiles (strong vs weak), regio- and 
        stereochemistry. 
    Corresponds to  content modules 07, 08A-B (D2L  content folder)   | 
  
  
    Wk 4 
    (Feb 3-7) | 
    Radical 
    addition of HBr to alkynes. 
    Hydration of alkenes : addition using H3O+ (i.e. aqueous acid) to give alcohols 
    Hydroboration 
    / oxidation of alkenes 
        Oxymercuration 
        / demercuration reactions of alkenes 
        Hydration 
        of alkynes to ketones (via enol tautomerism) 
        Hydroboration 
        / oxidation of alkynes. 
Corresponds to content modules 05B, 06A-D      (D2L  content folder)   | 
  
  
    Wk 3 
    (Jan 27-31) | 
    Catalytic hydrogenations of alkenes and alkynes. 
      Hydrohalogenation : addition of HX (HCl, HBr, HI) to alkenes to give alkyl halides (inc. radical addition of HBr)  
      Markovnikov's 
        Rule - origins of the empirical observation (i.e. intermediate stability). 
      Hydrohalogenation : addition of HX  to alkynes to give vinyl halides and alkyl dihalides. 
    Corresponds to content modules 04, 05A & B T    (D2L  content folder)   | 
  
  
    Wk 2 
    (Jan 20-24) | 
    etext Ch 7: Isomer types (review), optical activity, polarimetry, specific rotation. Fischer projections, D/L nomenclature 
      etext Ch 6 Addition 
        reactions of alkenes and etext Ch 9 addition reactions of alkynes 
        Start with a quick review of alkenes and alkynes: alkene nomenclature, alkyne nomenclature, structure, phys. properties, preparations of alkenes and alkynes. 
          Alkene and alkyne reactivities: what is their role in reactions ?  Introduction 
            to addition reactions. Transformations, regiochemistry, 
            and stereochemistry.  
    Corresponds to  content modules 02A, B & C (Optical Activity 1-3) + 03A & B (D2L  content folder)   | 
  
  
    Wk 1 
      (Jan 13-17) | 
    Introduction to Organic Chemistry 
      II. What to expect, what to do, what not to do etc. 
      A little review of a few issues : key concepts from 351 Organic 
        chemistry concept map, the families 
          of reaction mechanisms, learning reactions. 
      etext Ch 7: Isomer types (review) 
      Corresponds to content modules 00A & B ("Intro & Prep" ), 01 (Learning Reactions), 02A (Optical Activity 1) (D2L  content folder)  
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