Organic Chemistry
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Refer to the concerted reactions shown below. Identify the reaction with a more stable transition state and justify your answer.
Phenol is weakly acidic and can be deprotonated in basic solutions compared to cyclohexanol. The pKa of phenol is 10, while the pKa of cyclohexanol is 16. Explain why the pKa of phenol is lower than the pKa of cyclohexanol.
Why are all the carbon-carbon bonds in benzene of the same length (1.39 Å)? Note: The average bond length of C―C is 1.53 Å and C=C is 1.31 Å.
Shown below is the MO energy diagram of a cyclooctatetraene derivative. Does the MO energy diagram correspond to a stable or unstable configuration? Provide a brief explanation for your answer.
Suppose that Kekulé’s original hypothesis had been correct, identify the number of isomers that 1,2-dibromobenzene would have had.
Molecule I is expected to have a higher solubility in water than molecule II. Explain why.