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18 Cards in this Set
- Front
- Back
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pka of carboxylic acid around… b/c…
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4.5 - res stab of conj base
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carb acid boiling pt higher/lower than alcohol b/c…
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higher b/c can form 2 H+ bonds
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how to synthesize carb. Acid:
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oxidize primary alcohol (also with KMnO4), hydrolysis of nitrile, Grignard + CO2
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heating of B-keto carboxylic acid results in____
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decarboxylation
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how do you synthesize ald from carbox acid?
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can't! no direct route!
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dif b/w hemiketal and hemiacetal
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ketal = derived from ketone
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how form ketal?
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make hemiketal with 1 alcohol, acidify to lose an H20 (loses chirality) + add another alcohol
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aldol condensation occurs between and results in... proceeds by...
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between 2 ketones, results in a,b unsaturated aldehyde and water: make enolate (taut to enol, extract an H, make neg central C so forces x2 bond to attack another center) or by extract α-hydrogen, attack carbonyl --> acid workup --> h20+ and use base to elim water and make x2 bond
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Claisen Condensation
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like aldol condensation exept avail LG (kick off alcohol HOR) so retain both carbonyl O's (no dehydration)
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how do you make an ylide?
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CP + CH3Br --> C+PCH3 + Br- --> phosphonium salt --> deprot CH3 --> CH2- so you have a CP+ and CH2- in same molec
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basic mechanism of Wittig rxn
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replace carbonyl O with alkyl group via ylide
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Zaitsev and Hoffman products
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more vs less sub x2 bond (scoff at the hof b/c there's weaker x2 bond)
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unlike alcohols, ethers cannot ______ and so they have a _____ bp
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hydrogen bond, lower (comprable to alkanes)
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antiaromatic compound is___
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cyclic, condjugated, and has 4n π e-
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sulfonation of aromatic
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aromatic + SO3/H2SO4 --> add HSO3
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nitration of aromatic
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aromatic + H2SO4/HNO3 --> add NO2
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what's the difference between a nucleophilic and electrophilic rxn?
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nuc reacting with subst or electro reacting with substrate
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between ortho and para, what's the ratio of addition at each spot?
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66% ortho, 33% para (b/c 2 o spots vs 1 p spot) - no steric hindrance b/c planar
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