cyclohexanol synthesis by reduction

cyclohexanol synthesis by reduction - Synthesis of...

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Synthesis of Cyclohexanol by Reduction Tore Maras-Lindeman Drawer U337 • February 2011 • TA Matt Tore Maras-Lindeman • email: [email protected] • Student No. 10668240 1
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Synthesis of Cyclohexanol by Reduction Sodium Borohydride assisted reduction of cyclohexanone TORE MARAS-LINDEMAN Purpose The purpose of this experiment was to execute the synthesis of cyclohexanol from cyclohexanone by way of reduction using sodium borohydride. In essence, the actual yield of an alcohol by having the ketone react with the reducing agent, sodium borohydride. Furthermore, the yield of a pure product through the method of reduction was to tested via IR who’s IR spectra generated is to be compared to known spectra to determine if a pure sample was indeed collected, and if the reduction was successful. Theory Reduction, in organic chemistry is a vital method to synthesize alcohols. Ketones, are compounds with RC(=O)R*, structures. (R and R* are groups of atoms or different atoms). Basically, a ketone has a carbonyl group (C=O) which is bound to two other carbons. The actual carbon of a ketone is sp 2 hybridized. The structure of a ketone of the ketonic carbon is trigonal planar, forming carbon angles of approximately 120°. The structure of a ketone indicate that they acceptors of hydrogen bonds and soluble in water, evidently from the
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carbonyl groups interaction potential with water. Though, due to their structure, they are not, under normal circumstances hydrogen donors. Carbonyl groups are found within carboxylic acids, esters, aldehydes and ketones. Occurrences of carbonyl groups occur when the actual oxygen center’s electronegativity is stronger of the carbonyl atom and is depicted as a single carbon which is double bound to an oxygen (C=O). Though, in order to identify the compound as a group either that be an aldehyde or ketone, we must what else is bound to the carbonyl atom. If the carbonyl atom which is bound to an oxygen by a double bond is also bound to a hydrogen and an R group, then it is an aldehyde. Though, if the carbonyl carbon is bound to two other R groups as deFned earlier it is a ketone. Moreover, a group composed of hydrogen bound to an oxygen via a single bond (R-O-H) is an alcohol group. Thus, it is a matter of “reduction of bonds”, when transforming a ketone to an alcohol, where the carbonyl group is breaking that double bond with the oxygen, and forming a single one, and in turn the yield of an alcohol will manifest(Hart 2006). This occurs with the presence of two hydrogens, where one hydrogen will bond with the oxygen and the other with
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This note was uploaded on 04/11/2011 for the course CHE 231 taught by Professor Patwardham during the Spring '08 term at Kentucky.

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cyclohexanol synthesis by reduction - Synthesis of...

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