Advanced A Level Organic Chemistry: Reaction mechanisms - hydride reduction of aldehydes/ketones
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Doc Brown's GCE Chemistry - Revising Advanced Level Organic Chemistry - GCE A Level Revision Notes PART 10 Summary of organic reaction mechanisms - A mechanistic introduction to organic chemistry and explanations of different types of organic reactions
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10.6 Aldehydes–Ketones - Reduction with hydrides
10.6 Carbonyl compounds – ALDEHYDES and KETONES
10.6.1 Introduction to aldehyde and ketone reactivity
Aldehydes and ketones readily undergo nucleophilic attack because of the highly polar carbonyl bond >Cδ+=Oδ– caused by the big difference in the electronegativity between carbon (2.5) and oxygen (3.5). An electron pair donating nucleophile (Nuc:), will therefore attack the 'positive carbon' (Cδ+) to form a C–Nuc bond. A comparison of electrophilic addition to alkenes with nucleophilic addition to aldehydes/ketones is included in these notes.
10.6.3 Nucleophilic addition of a hydride ion in the reduction of aldehydes/ketones to primary/secondary alcohols
mechanism 40 – nucleophilic addition of a hydride ion (via NaBH4 or LiAlH4) to an aldehyde or ketone
keywords phrases: reaction conditions formula intermediates organic chemistry reaction mechanisms nucleophilic addition elimination nucleophilic substitution NaBH4 sodium tetrahydridoborate(III) LiAlH4 lithium tetrahydridoaluminate(III) (OH)CN RR'C=O + 2[H] ==> RR'CHOH XH4– + R2C=O => [H3XO–CHR2]– = R2C=O => [H2X(O–CHR2)2]– = R2C=O => [HX(–OCHR2)3]– = R2C=O => [X(–OCHR2)4] – [X(OCR2)4]– + water/acid/alcohol => 4R2CHOH
APPENDIX - COMPLETE MECHANISM and Organic Synthesis INDEX (so far!)
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