notes5 - BP ( ° C) Sol in H 2 O CH 3 CH 2 OH ethanol 46 78...

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Comparison of boiling points and water solubilities for molecules with different functional groups. Each table shows two or more compounds of approximately the same molecular weight (MW) and shape; they differ in functional group. The table shows the boiling point (BP) and solubility in water for these compounds. Each table is in order of decreasing boiling point. Note that solubility trends are sometimes less clear than BP trends; this is for the same reason Your main goal for (almost) any pair of compounds of similar MW, you should be able to predict which has the higher BP, and explain why. Tables are, in part, based on similar Tables in a previous textbook, Bettelheim et al, Introduction to General, Organic, and Biochemistry, 6/e, 2001. I. Alcohol vs alkane (Bettelheim 6/e Table 13.1) Structure Name MW
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Unformatted text preview: BP ( ° C) Sol in H 2 O CH 3 CH 2 OH ethanol 46 78 infinite CH 3 CH 2 CH 3 propane 44-42-II. Alcohol vs ether (Bettelheim 6/e Table 13.2) Structure Name MW BP ( ° C) Sol in H 2 O CH 3 CH 2 OH ethanol 46 78 infinite CH 3 OCH 3 dimethyl ether 46-24 + III. Acid vs alcohol vs aldehyde (Bettelheim 6/e Table 18.2) Structure Name MW BP ( ° C) Sol in H 2 O CH 3 COOH ethanoic acid 60 118 infinite CH 3 CH 3 CH 2 OH 1-propanol 60 97 infinite CH 3 CH 2 CHO propanal 58 49 ++ IV. Many groups (Bettelheim 6/e Table 17.2) Structure Name MW BP ( ° C) Sol in H 2 O CH 3 CH 2 COOH propanoic acid 74 141 infinite CH 3 CH 2 CH 2 CH 2 OH 1-butanol 74 117 + CH 3 CH 2 COCH 3 2-butanone 72 80 +++ CH 3 CH 2 CH 2 CHO butanal 72 76 + CH 3 CH 2 CH 2 CH 2 CH 3 pentane 72 36-CH 3 CH 2 OCH 2 CH 3 diethyl ether 74 34 + 402/physcomp 8/23/06 + = 5-10% (by wt.) ++ = 10-20% +++ = 20-30%...
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This note was uploaded on 07/21/2011 for the course CHEM 111 taught by Professor Sawyers during the Spring '11 term at Virginia College.

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