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THINGS YOU HAVE LEARNED FROM LAST TWO MODULES which are important for this module. Resonance Acid/base properties Conjugation Aromaticity. Nucleophile/electrophile Curly arrows/pushing electrons Nucleophilic substitution Sn1, Sn2 Elimination E1, E2, E1CB Electrophilic addition
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THINGS YOU HAVE LEARNED FROM LAST TWO MODULES which are important for this module Resonance Acid/base properties Conjugation Aromaticity Nucleophile/electrophile Curly arrows/pushing electrons Nucleophilic substitution Sn1, Sn2 Elimination E1, E2, E1CB Electrophilic addition Diels-Alder Reaction WHAT IS NEW IN THIS MODULE Reaction of carbonyl compounds (most of this module) Electrophilic subsitution (small part – reaction of benzene compounds) Application to biochemical reactions (small part – reaction of benzene compounds)
SUMMARY OF MOST OF THIS MODULE THE MAIN PROPERTIES OF THE CARBONYL GROUP Point 1 C=O is a p---- co------- bond C is d+ - attractive to nu---------s O is d- - attractive to pr---ns (ac--ds) Point 2 C=O – -- bond (type) The p bond is w---er and usually breaks first Point 3 The carbonyl group is tr-----l pl----r i.e. it is flat Point 4 The C-H bond (the a hy------n) is ac----c – breaks easily - to form an an--n
SUMMARY OF MOST OF THIS MODULE Point 4 The C-H bond (the a hy------n) is ac----c – breaks easily - to form an an--n Chapters 22 and 23 RHS is itself nu-------le – lone pair electrons Can react with other electrophilic molecules e.g. RHS is stabilised by resonance BACK
SUMMARY OF MOST OF THIS MODULE Note 1 – notice change in hy--------n and ge-----y Chapters 19 and 21 Note 2 – notice Nu can come from either side Generally racemic products are produced Point 1 C=O is a polar covalent bond C is d+ - attractive to nucleophiles Point 2 C=O – p bond The p bond is weaker and usually breaks first Point 4 The carbonyl group is trigonal planar i.e. it is flat
SUMMARY OF MOST OF THIS MODULE Part 1 19.5, 19.6, 19.7, 19.10 Part 3 Ch 21 Important – ester, amide hydrolysis Part 2 19.8, 19.9 and 19.11
SUMMARY OF THIS LECTURE Part 1 19.5, 19.6, 19.7, 19.10 19.5 Nu = H2O – acid & base 19.6 Nu = CN- 19.7 Nu = R- 19.10 Nu = ROH Mechanisms all essentially same (19.6 easiest) – but must practice moving H+ - 19.7 must take note of role of MgX
SUMMARY OF THIS LECTURE 19.4 - reminder what is nucleophile (bottom p 702- top 703) - geometry – nucleophilic must attack from a certain angle - which aldehydes/ketones are more reactive - steric reason (middle p 703) - electronic reason (bottom p703 to top p 704) 19.6 - cyanohydrin – mechanism middle p 707 – classwork 19.44 (wider significance – addition of C to skeleton) 19.5 - water – mechanism alkaline (fig 19.4), acidic (fig 19.5) catalysis Problem 19.8 19.5 - Grignard reaction – mechanism (fig 19.6) – classwork 19.37 (a) (wider significance – addition of C’s to skeleton) – did not cover in this lecture 19.10 - acetal formation – mechanism (fig 19.12) – classwork 19.39 Homework 19.39,19.43