Organic Chemistry
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In contrast to the reaction (i), reaction (ii) predicts the formation of a thioether. Explain this phenomenon.
Acetone can be used as a solvent in the reaction between an alkyl bromide and potassium iodide to increase the amount of alkyl iodide formed. Explain. (Hint: Potassium iodide is soluble in acetone but potassium bromide is not.)
Why does a nucleophilic reagent, such as methoxide ion, add more easily to an alkyne than an alkene?
Determine the products of the following reactions.
a. CH3Br + CH3CH2O−
b. CH3Br + HC≡C−
a. CH3Br + CH3CH2N(CH3)2
b. CH3Br + CH3CH2S−
The synthesis of 2,3-dihydrobenzo[b][1,4]dioxine-2,3-dicarboxylic acid is illustrated here:
Illustrate the mechanism and determine the intermediate (A).
Allyl chloride is an important industrial compound. Large quantities of allyl chloride are used to produce epichlorohydrin, a precursor to many epoxy resins. Allyl chloride reacts with many nucleophiles to give nucleophilic substitution reactions. An alkyl halide that is similar in structure to allyl chloride is propyl chloride. If both of these compounds react with sodium methoxide, which is less likely to be consumed first?
For the following substitution reactions, determine which would react faster.
(CH3)3CCH2CH2Cl + H2O or (CH3)3CCH2CH2Cl + HO−
Predict the products of the reaction shown below.