Part I
For the first four questions, show the starting material, reagent, and product. No arrows or intermediates are required. Keep it simple!
1.Give an example of a reaction that would have an SN1 mechanism
2.Give an example of a reaction that would have an SN2 mechanism
3.Give an example of a reaction that would have an E1 mechanism
4.Give an example of a reaction that would have an E2 mechanism
Part II Nomenclature
5.Supply the missing name or structure
Part III Mass spectroscopy
6.An alcohol of unknown structure has been analyzed as C14H22O and is suspected of being a tertiary alcohol.
a) What are the degrees of unsaturation (HDI) for this formula? Show your calculation.
b) Which one unsaturated group (considered a standard functional group) does this HDI suggest?
c) The most prevalent fragmentation peaks for this alcohol in El MS are M-29, M-57, and M-91. Identify the free radical that is lost to form each of these fragments
d) Give any one of the possible structures for this alcohol consistent with this data.
e)Show the mechanism for the fragmentation of the radical cation of this alcohol to give any one of the possible fragments that is detected in the mass spectrum of this alcohol.
7. Provide reagent for each transformation
8. Give the product to each of the following transformations
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10. Give the seven possible isometric products of the following reaction
Give the detailed mechanism for the following reaction
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