Question

An amide is typically drawn with a single bond connecting the carbonyl C atom to the N atom. If this representation were accurate, we would expect the N atom to be pyramidal, and we would also expect C-N to undergo free rotation. In actuality, however, the N atom is rather planar, with the bond angle close to 120 degree, and the rotation is quite hindered Explain this surprising finding (if resonance is part of your answers, draw the pertinent resonance structures). Also draw the orbital picture of the acetamide molecule to represent the actuality that N atom is rather planar. Jim works in Dr Peterson's Lab, he ran out 1,2-dichloroethene so he went to borrow 1,2-dichloroethene from Dr Wiseman's Lab Just about to use the chemical from Dr. Wiseman's lab, he looked at the label on the two bottles and found out that the two bottles have the same chemical name, same chemical formula but the boiling point of the two bottles are different. The one in his lab has the boiling point of 60.3 degree C and the one from Dr Wiseman's lab has the boiling point of 47.5 degree C. He decided to check the CRC Handbook for the reference boiling point of 1,2-dichloroethene. Later he found out that the chemical in both bottles is indeed 1,2-dichloroethene with the difference in the boiling point. What is missing in label that should have been done to distinguish between the two bottles? How would you explain the difference in boiling point of 1,2-dichloroethene from the two bottles?

Answer 1

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