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orgo 2 exam 2
Terms in this set (12)
why do carbox acids have higher boiling points than most molecules?
•Result from their polarity and their ability to form very strong intermolecular hydrogen bonds
why are carboxylic acids more soluble in water than alcohols, ethers, aldehydes, and ketones?
•Result of forming hydrogen bonds with water molecules through both their C=O and OH groups
why does solubility decrease in water was you increase hydrophobic chains?
becomes less polar
acetic acid pka
why are carboxylic acids more acidic than alcohols?
•Delocalization of the negative charge of the carboxylate anion through resonance
How can electron withdrawing groups affect the acidy of carboxylic acid? And how do you call this effect? And how can the distance of EWG affect the pka of carboxylic acid?
•Electron-withdrawing inductive effect of the carbonyl group
-ewg presence makes carbox more acidic
-greater distance between EWG and rest of molecule makes it less acidic (more stable, less able to donate protons)
how to increase the yield of fischer esterification reaction?
take away water and use hella alcohol (excess drives rxn to the right)
Why use the alcohol in excess in the reaction of esters formation?
produces high yield
IUPAC naming of carboxylic acids
why is the claisen condensation not catalytic?
in claisen condensation you form the beta-keto ester 2 times. Add acid at the last step to form the 2nd beta-keto ester. Why?
reprotonate alpha carbon
why is the Dieckmann condensation not catalytic?
acid is not reformed at the end
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