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Moiz_6047
#1 Posted : Tuesday, July 27, 2021 10:15:48 PM
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14) Would really appreciate some help with this section. Because amides contain Nitrogen they would be considered weak bases right, and therefore we would add HCl ? Or are all carboxylic acid derivatives considered weak acids? Also, because amines are bases, couldn't we add HCl to make it part of the aqueous layer? (option D). What does it mean to "quench unreacted anhydride"?

20) The text mentions that "The researchers mixed liposomes of different sizes and observed that those formed from Compound 1 were stable to mixing" therefore, wouldn't compound 1 be thermodynamic as it is more stable?
INSTR_Molly_129
#2 Posted : Saturday, July 31, 2021 9:08:37 PM
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Hi Moiz,

14) Not quite. The lone pair electron engage in resonance and is a terrible base. A reaction between amine and acid anhydride would result in an acidic by-product. Quench here means to remove any remaining starting material, in which case, the anhydride. Addition of base or acid will convert anhydride to carboxylic acid, but the choice is key for separation. Addition of base will make all anhydride and byproduct acid charged, pushing it to aqueous phase. Amide will remain in the organic phase. Choice A was the best answer.

20) At first it might seem like that, but actually, compound 2 was under thermodynamic control, given that it is forming new liposomes and attaining the most stable conformation, while compound 1 was making the liposomes as fast as it can, therefore it is stable to mixing.

Hope that helps,

Molly
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