1) Consider respect the to following substitution reactions and associated rate data and discuss
increase the rate mechanism and two that (i.e. would analyze decrease the data). it for Also, each propose reaction. two solvents briefly that would
Nu + SPh2
Ph = Phenyl
Rate of reaction (105 k, St1) of nucleophiles (Nu) with PhCH,StPh
Nucleophile: AcO Cr PhO HO PhS
Relative rates of reaction (water = 1) of nucleophiles (Nu) with MeBr:
2) Provide mechanistic rationale for the following two transformations and discuss.
3) of dimethyl sulfate. product(s), Please any, provide mechanistic rationale, including movement
Predict the if when phenol is treated with sodium hydroxide in of the electrons presence and
resonance structures (note: none of these compounds are solvents).
4) Which reaction is best suited for the preparation of the following ether: (CH3)SCOCH2CH3
CH3CH2Br + (CH3)3COK
(D) (CH3)3CMgBr + CH3CH2OH
or water, using arrow pushing, indicate the mechanism by which this common intermediate
5) Both of these amines undergo a similar reaction in either the presence of sodium hydroxide
forms and draw its structure. In determining the structure of this intermediate, consider the
he structures of the two products, consider the reactivity of sodium hydroxide and water and the
of the functional groups on these molecules and how they might react. In determining
substitution reaction mechanisms that they each promote. Draw
of each product, and discuss.
a mechanism for the formation
6) Please provide the product(s), if any, of the following reactions. If there is more than one
product, indicate which will be major and which will be minor. Also, using mechanistic rationale,
discuss the relative rates of reaction of these two sube tituted cyclohexanes.
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