4) sketch what a developed and resolved TLC plate of a mixture of benzil, benzoin and...
4) sketch what a developed and resolved TLC plate of a mixture of benzil, benzoin and hydrobenzoin might look like. Discuss the relative Rf values on your sketched plate
5) In the reduction of benzil with sodium borohydride, 3 compounds are possible: meso-hydrobenzoin, racemic-hydrobenzoin and racemic-benzoin (resulting from incomplete reduction of benzil). Discuss how you determined (or will go about determining) which of these products was produced. Discuss evidence from melting points, TLC and IR spectra.
Homework Answers
4)
compare to benzil, benzoin is more polar because in benzoin hydroxyl group has a charge differential between the oxygen and hydrogen. similarly compare to benzoin, hydrobenzoin in more polar due to the presence of two hydroxy group.
least polar to more polar
benzil > benzoin > hydrobenzoin
5) The IR of meso-hydrobenzoin and racemic hydrobenzoin will have peak broad peak at 3300 cm-1 due to the presence of hydroxy group. whereas racemic benzoin will have peak at 1700 cm-1 and 3300 cm-1 due to the presence of carbonyl group and hydroxy group respectively.
whereas meso hydrobenzoin and racemic hydrobenzoin are diastereomers will have different melting point. and in TLC meso hydrobenzoin and racemic hydrobenzoin will have very less polarity difference.
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4) sketch what a developed and resolved TLC plate of a mixture
of benzil, benzoin and...
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