CHEM 0320 Study Guide - Midterm Guide: Nucleophile, Trigonal Pyramidal Molecular Geometry, Organolithium Reagent
Document Summary
Due to h bonding, carboxylic acids exist as dimers: carb. Acids are highly water soluble: carb acids have high melting & boiling points. Element effect: o is more electronegative than c, so o is better at stabilizing and having (-) charge: stable conj. Acidic conditions = strong electrophiles & weak nucleophiles. Basic conditions = weak nucleophiles & strong electrophiles. Factors affecting rate of snac: l. g. ability/stability of conj. Base: resonance stabilization of carbonyl c (before nucleophilic attack, electronegativity/inductive withdrawing effect (this effect not as large as first two) Amides are extremely unreactive; bad for synthesis. Lda = good base, very poor nuc (lots of sterics) Acyl chlorides & anhydrides are electrophilic enough to be attacked directly without prior protonation of the carbonyl. When concentrated strong acid is used, protonation of the amine nucleophile is favored over ester. Ketone + 1) nabh4 2) acid or water alcohol: nabh4 only reduces ketones/aldehydes, lah reduces everything with c=o.
