CHM 2120 : 2120 Blackboard problem set 5 Aldol and related reactions ANSWERS.pdf
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Chm 2120 problem set 5 -- answers. **take a look at the description of expectations for synthesis problems in the last question. Note: many questions incorporate earlier material: draw the mechanism for the tautomerization of 1-phenyl-1-butanone (also known as butyrophenone and phenyl propylketone) by, acid catalysis, base catalysis, acid (ha) Ir: keto form: would see c=o stretch (peak) at about 1715 cm-1 -- not observed enol form (phenol): would see the broad oh stretch (peak) at about 3200 cm-1 - observed more stable tautomer is aromatic. Answers: draw a mechanism for the generation of the compounds shown below. Describe how the 1h nmr of the starting material would differ from the 1h nmr of the two products. Note: h = 1h detected by 1h nmr (peaks are seen) D = 2h not detected by 1h nmr (no peaks) = 1-1. 6 ppm doublet (only sees 1 h neighbor; the d is not observed)
