1.You find to your surprise that the reaction of phenol withacetic anhydride and aluminum trichloride gives a mixture of twodisubstituted products. Pick the best reason for why.
A.The OH oxygen reacts twice to give the bisesterderivative.
B.Ring acylation occurs twice in the ortho-ortho' and ortho-parapositions.
C.The first acylation product is in the ortho and para positionswhich deactivates the ring and causes meta-substitution with thesecond acetyl group to give ortho-meta and meta-paradiacetylphenols.
D.The first reaction is at the oxygen to give phenyl acetatefollowed by acetylation in the ortho and para positions to give amixture of products.
2.Compare the reactivity of the oxygen to acetylation withacetic anhydride for phenol versus cyclohexanol by picking the bestanswer below.
A.Electron donation by the cyclohexane ring increasesnucleophilic attack by the oxygen of cyclohexanol versusphenol.
B.Resonance is greater for the phenol acetyl oxoniumintermediate than for the cyclohexanol analog.
C.Base catalyzed formation of the phenolate is faster than forcyclohexanol due to resonance stabilization, and the anion formedis more reactive.
D.In fact, they both react at the same rate.
3.EAS reactions involve attack by something seeking:
A.all of the below.
B.electrons, and those are almost always relatively \"available\"ones in pi-orbitals.
C.a nucleus to bond to, making the reaction also a\"nucleophilic\" attack.
D.a one-step reaction involving loss of leaving group at thesame time the attacking group makes a new bond.
4.All EAS reactions involve a \"tetrahedral\" or Td intermediate.Which of the following is true of this statement?
A.Can't happen with an aromatic ring carbon which by definitionis sp2 or trigonal planar.
B.There is no intermediate in EAS which simple involves attackat electrons.
C.No, the leaving group leaves at the same time the attackinggroup forms a bond.
D.Almost all do: an sp2 carbon becomes sp3 in theintermediate.
