Chem 353 Weekly Bulletin

CHEM 353 WEEKLY BULLETIN

Chem 353 Organic Chemistry II, W24
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The best preparation for Chem 353 is a solid grasp of all that went before, especially the core concepts from Chem 351: you will need to know those materials.

Here is the link to the Chem 353 semester calendar

Chem353W24 wk 13 (Apr 8-9 2024):

CHEM353W24 MT solutions are posted in the "exam archive"

CHEM353W24 FIN Tuesday April 16th 2024, 09:00-11:00 GOLD GYM (see D2L News item for more information about the final exam)

Note :
An end of semester warning ! Be very cautious about micro-managing grades and if you feel that you must, do it as points currently acquired and don't be mislead by a current "%" (i.e. "I had 80% going into the final ") which is untrue since the Final is worth 35% meaning that the max going in would have been 65%, and what they meant was that they had 80% of 65 = 52 % which tells a very different story.

LABORATORY

Questions or concerns about laboratory related issues ? Contact the Chem353W24 laboratory coordinator, Dr Causton.
Chem353W24 student laboratory manual.

The laboratory component total grade will be posted in the D2L gradebook once ALL the grading is completed by the laboratory TAs and the grades have been compiled. You can check reports grades in feedback on each graded report and quizzes / worksheets in Moodle. Your TA should have given you your pre-lab and notebook grades. The breakdown of laboratory grades is in section 6 "Grading for the laboratory" on p4 of the Chem353W24 laboratory manual

CAL TUTORIALS

Questions or concerns about tutorial related issues ? Contact the Chem353W24 course coordinator, Dr Hunt.
The tutorial component completed last week. CAL 5 grades will be posted to the D2L gradebook in the near future (as time allows), CAL1-4 are already there.

L01 LECTURE topics week by week (the etext links are the potentially valuable details here). The yellow row represents the current week and the table will grow each week to provide a record of where we have been.

Wk 13 (Apr 8-9)	Tuesday Apr 9 2024 is the last day of classes. 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 37a1, 37a2
Wk 12 (Apr 1-5)	Easter Monday (Apr 1) is a holiday and UofC is closed, no classes. etext Ch 17 :The Baeyer-Villager oxidation / reaction etext Ch 19 : Carboxylic acids - reactions to prepare 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 Corresponds to L01 content modules 35a2, 36a1, 36a2 (D2L L01 content folder)
Wk 11 (Mar 25-29)	Good Friday (Mar 29) is a holiday and UofC is closed, no classes. 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. Corresponds to L01 content modules 33, 34, 35a1, 35a2
Wk 10 (Mar 18-22)	etext Ch 12 : How do aromatic substituents influence reactivity ? Substituent effects, understanding, rationalising and recognising 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 L01 content modules 29, 30, 31, 32 & 33 (D2L L01 content folder)
Wk 9 (Mar 11-15)	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. 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 CH₂Reactions 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 ? (contd) Corresponds to L01 content modules 26, 27 & 28 (D2L L01 content folder)
Wk 8 (Mar 4-8)	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 L01 content modules 23, 24, 25 & 26 (D2L L01 content folder)
Wk 7 (Feb 26-Mar 1)	etext Ch 10 Polyenes: Terminology - conjugation, resonance, allylic systems : reactivity 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 L01 content modules 19, 20, 21, 22 (D2L L01 content folder)
Break (Feb 19-23)	UofC WINTER SEMESTER BREAK (no classes)
Wk 6 (Feb 12-16)	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 (18 no audio, just a table to complete from notes "review") Corresponds to L01 content modules 15, 16, 17, & 18 (D2L L01 content folder)
Wk 5 (Feb 5-9)	Halogenations of alkenes and alkynes Halohydration (reactions with X2 / H2O and HOX) of alkenes. 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. Ozonolysis of alkenes and alkynes considering both oxidative and reductive work-ups. Corresponds to L01 content modules 12, 13, 14 & 15 (D2L L01 content folder)
Wk 4 (Jan 29-Feb 2)	Hydration of alkenes : addition using H3O+ to alcohols Hydroboration / oxidation of alkenes Oxymercuration / demercuration reactions of alkenes Hydration of alkynes to ketones (via enol tautomerism) Hydroboration / oxidation of alkynes. Halogenations of alkenes and alkynes Corresponds to L01 content modules 08, 09, 10, 11, 12 (D2L L01 content folder)
Wk 3 (Jan 22-26)	Catalytic hydrogenations of alkenes and alkynes and dissolving metal reduction of 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. Radical addition of HBr to alkynes. Hydration of alkenes : addition using H3O+ to alcohols Corresponds to L01 content modules 05, 06, 07, 08 (D2L L01 content folder)
Wk 2 (Jan 15-19)	A quick review of a few issues relating to reactions: key concepts from 351 Organic chemistry concept map, the families of reaction mechanisms, learning reactions. 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. Catalytic hydrogenations of alkenes and alkynes. Corresponds to L01 content modules "Intro & Review" 351 rxn summary plus 03, 04 & 05 (D2L L01 content folder)
Wk 1 (Jan 8-12)	Introduction to Organic Chemistry II. What to expect, what to do, what not to do etc. etext Ch 7: Isomer types (review), Optical activity, polarimetry, specific rotation. Fischer projections. Corresponds to L01 content modules optical activity_01, _02, _03 (D2L L01 content folder)

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