94年私立輔仁大學化學所(甲組)有機化學

Explain the following terms:

1. allylic protons
2. oligomer
3. terminal acetylenes
4. Clemmensen reduction
5. diastereomers
6. racemate
7. nucleophile
8. Williamson ether synthesis
9. Claisen condensation
10. iodoform test

Which of the alkene shown below violate Bredt’s rule and unstable?

Which molecule shown below has R configuration?

In which compound is the indicated unshared pair of electron not a contributorto the aromatic system?

Propose the mechanism for the following reactions.

Determine the structure of pinene, and the reaction products of (A), (B), (C),(D).

Show how you would accomplish the synthetic conversion. Show allintermediate products and all reagents.

An unknown compound with a formula of C₆H₈O give the following IR and^₁H/¹³C NMR spectra.Propose a structure for the unknown compound.