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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