Question

This experiment was based on Aldol-dehydration reaction using unknown aldehydes and ketones. We carried out an aldol condensation between an unknown aldehyde and an unknown ketone. Here are the list of possible unknown aldehydes and ketones that were used.

You will be assigned a ketone and an aldehyde from the following list of starting reagents for your aldol condensation. 요 acetone cyclopentanone cyclohexanone 4-methylcyclohexanone cycloheptanone H H CHO CHO Meo benzaldehyde 4-methylbenzaldehyde (p-tolualdehyde) 4-methoxybenzaldehyde p-anisaldehyde E-3-phenylpropenal (cinnamaldehyde) 2-furaldehyde (furfural) Table of melting points for the aldol-dehydration products formed from the reaction of the above ketones and aldehydes. Ketone Aldehyde acetone cyclopentanone cyclohexanone 4-Me-cyclohexanone cyloheptanone benzaldehyde 113 °C 189-190 °C 118-119 °C 98-99 °C 106-107°C tolualdehyde 175 °C 233-235 °C 170 °C 134-136 °C 131-133°C anisaldehyde 129-130 °C 212-214°C 160-162 °C 136 °C 128-129°C cinnamaldehyde 144-145 °C 223-225 °C 180-181 °C 163-164 °C 198-199°C 2-furaldehyde 166-168°C 145-146°C 96-97°C 114°C

Here is the NMR of the final product. Please predict the structure given the melting point is 163 degrees Celsius. The analysis of the 1H NMR spectrum should include a detailed assignment of each of the NMR resonances to the protons found in your structure. NMR analysis should include reasoning used to exclude other aldehydes and ketones from your structural assignment.