l07 - CH 203 O R G A N I C C H E M I S T R Y I...

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Constitutional isomers © Bruno I. Rubio 1 CH 203 O R G A N I C C H E M I S T R Y I Constitutional isomers Constitutional isomers An organic molecule’s properties (e.g., molecular weight, melting point, boiling point, reactivity, color, odor, etc.) depend not only on how many and what kind of atoms make up that molecule, but also on the manner in which that molecule’s constituent atoms are linked one to another. Consider the formula C 4 H 8 O 2 . Four C atoms, eight H atoms, and two O atoms can combine in a vast number of ways: different arrangements of these atoms re- sult in different compounds with different properties. Three possibilities are shown below: H O O CH 3 • Propyl formate (boiling point 80 °C, melting point –93 °C) occurs naturally in currant, pineapple and plum. Because of its sweet smell (like rum with berry notes), it is used to make perfume. H 3 C OH O • Butyric acid (boiling point 164 °C, melting point –5 °C) is found in vomit and rancid butter. Nobody’s making perfume out of this!
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This note was uploaded on 02/27/2012 for the course CH 203 taught by Professor Rubio during the Fall '07 term at BU.

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l07 - CH 203 O R G A N I C C H E M I S T R Y I...

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