ELECTROPHILIC AROMATIC SUBSTITUTION: NITRATION OF A MONOSUBSTITUTED ARENE
- Why are concentrated acids used in nitration experiments?
- The pKa values for sulfuric and nitric acids are -3 and -1.3. Which acid is stronger? Given your prediction, write a chemical equation for the equilibrium involving the reaction of sulfuric and nitric acids. What is the Keq for this acid-base reaction? Assume that the pKa of the conjugate of nitric acid is -13.
- Why are no di or trinitrated products formed in significant amounts in nitration of bromobenzene reactions? If you wanted to produce greater quantities of di and trinitrated products, what changes could you make to experimental conditions?
ELECTROPHILIC AROMATIC SUBSTITUTION: RELATIVE RATES OF REACTIONÃƒâ€šÃ‚Â
- Why does performing some Se2 reactions at 0 degrees Celcius allow you to identify the order of reactivity more definitively?
- Would you expect the relative rate of Se2 reactions to be faster or slower if molecular Chlorine were used instead of molecular Bromine? Explain your reasoning.
- Which compound would you expect to undergo bromination faster, aniline or acetanilide? Anilinium ion or aniline? Explain your reasoning.
REDUCTION OF CARBONYL COMPOUNDS: PREPARATION OF FLUORENOLÃƒâ€šÃ‚Â
- Sodium borohydride is fairly unreactive toward methanol, but adding a mineral acid to this solution results in the rapid destruction of the borohydride. Explain.
- What gas is evolved when sulfuric acid is added to the reaction mixture?
- 9-Fluorenone is colored, but 9-fluorenol is not. Why?
ALDOL CONDENSATION: PREPARATION OF TRANS-p-ANISALACETOPHENONE
- Explain why trans-p-anisalacetophenone would be expected to be more stable than the corresponding cis isomer.
- Propose a synthesis of cinnameldehyde using a mixed-aldol reaction.
- Write structures for the various aldol condensation products you expect from the aldol self-condensation of 2-butanone.
- How might primary, secondary, and tertiary alcohols be prepared from a Grignard reagent and suitable carbonyl-containing compound? Write chemical reactions for these preparations using any starting materials you wish (including the Grignard reagent) -- indicate stochiometry where important.
- Why is it unwise to begin addition of the solution of methyl benzoate to the Grignard reagent before the latter has cooled to room temperature and then plaed in an ice-water bath?
- The yield of benzoic acid obtained when only enough acid is added to the aqueous solution of sodium benzoate to bring pH to 7 is lower than that obtained if pH is brought below 5. Explain why.
Procedures come from Experimental Organic Chemistry by Gilbert and Martin.
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