Benzene

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TUTORIAL 1: STK1503 BENZENE AND AROMATIC 1. Draw structures corresponding to the names given. a. m-fluoronitrobenzene b. p o-chlorophenol c. o-chlorophenol d. 3,5-dimethylbenzoic acid e. 1-phenyl-3-methylpentane 2. Provide correct IUPAC names for each of the following compounds. a. NO2

CH3

b.

c.

CH3

d.
NH2 H2N CH3

e.

Ph C H3 C C

CH2CH2CH3 Ph

3. For each molecule below, predict whether the molecule would be expected to show aromatic character or not. Explain your answer in each case.

a.

O N N H

b.

OH + O

c.

d.

N O

4. Consider the data below to answer the following questions. base CH3 _ CH
2

Q
and H2C CH3 base H2C

QB

_ CH2

Z

ZB

Conjugate bases QB and ZB are both resonance stabilized. Draw the indicated number of resonance forms for QB and ZB.

_ CH

2

QB

H2C _ CH2

ZB

Which of the compounds above, Q or Z, would you predict to be most acidic? Explain your answer. 5. Most alkyl halides are nonpolar covalent compounds and, therefore, are soluble in nonpolar solvents and insoluble in water. Cycloheptatrienyl bromide is an unusual alkyl halide in that it is insoluble in nonpolar solvents, but is readily soluble in water! This behavior is consistent with cycloheptatrienyl bromide being an ionic compound. Why does cycloheptatrienyl bromide exist as an ionic compound? Explain by comparing the covalent structure to the ionic structure.

6 Provide a diagram which depicts the relative energies of the π molecular orbitals of benzene. Show which molecular orbitals are filled in benzene's ground state.

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