Kaplan FL 3 (paper) Question

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Psychotropic

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I don't quite understand the reasoning behind the answer explanation for 152 (bio section). Basically, this is an organic passage with three aromatic compounds listed in one of the figures. The first compound has hydroxide groups, the second compound is an azo dye with a primary amine group and the third compound has a tertiary amines. The question basically asks us to identify which of these compounds would hydrogen bond to cellulose (a polymer of glucose).

The answer states that only the first two compounds can bond. The third one can't because tertiary amines cannot hydrogen bond to the glucose hydroxide groups. This is where I am not sure if the problem is wrong, or if I am wrong...since tertiary amines have a lone electron pair, can't they hydrogen bond with the hydrogen of the hydroxide group?


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I don't quite understand the reasoning behind the answer explanation for 152 (bio section). Basically, this is an organic passage with three aromatic compounds listed in one of the figures. The first compound has hydroxide groups, the second compound is an azo dye with a primary amine group and the third compound has a tertiary amines. The question basically asks us to identify which of these compounds would hydrogen bond to cellulose (a polymer of glucose).

The answer states that only the first two compounds can bond. The third one can't because tertiary amines cannot hydrogen bond to the glucose hydroxide groups. This is where I am not sure if the problem is wrong, or if I am wrong...since tertiary amines have a lone electron pair, can't they hydrogen bond with the hydrogen of the hydroxide group?


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Tertiary amines don't have the characteristic hydrogen bond like x'tics. the nitrogen is not attached directly to any hydrogens and this lets it deviates. For a hydrogen bond molecule it must have a partially negative end and a partially positive proton like in H2O and tertiary amines disobey. Primary and secondary amines can however hydrogen bond with other molecules like H2O.
 
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