Chem 353 Weekly Bulletin
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CHEM353 WEEKLY BULLETIN
Chem 353 Organic Chemistry II, W25
 last modified : 

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

CHEM353W25

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.

LABORATORY

CAL TUTORIAL

LECTURE topics week by week (the etext links are the potentially valuable details here).

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, estersActive 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)

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 7Isomer types (review), optical activitypolarimetry, 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 7Isomer types (review)

Corresponds to content modules 00A & B ("Intro & Prep" ), 01 (Learning Reactions), 02A (Optical Activity 1) (D2L content folder)


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