Aromatic Compounds and Electrophilic Substitution

1. Provide structures for these compounds.
(a) p-nitrobenzoic acid (b) 3, 5-dimethylcychohexanone

(c) N-methyl-2,3-dimethylhexanamide (d) 4-ethyl-2-propyloctanoic acid

3. Order the following compounds in order of increasing reactivity (1 being the most reactive.

(a) CH3CONH2 ______ CH3COCl_______ CH3COOCH3________

(b) CH3COH_______ CH3CH2COH_______ (CH3)2CHCOH _______

4. For the following groups, provide whether the substituent is activating (A) or deactivating (D) as well as ortho-para (O-P) or meta (M) directing. Write A, D, O-P, or M in the appropriate spaces.

Group Activating/Deactivating O-P or M directing

-NO2 _________________ ______________

-Cl _________________ ______________

-CH2CH3 _________________ ______________

-CN _________________ ______________

-OH _________________ ______________

-NH2 _________________ ______________

5. Cycloheptatrienone is a stable polar compound, but cyclopentadienone, although polar, is so reactive that it cannot be isolated. Briefly explain.

6. Circle which of the following is more stable. Explain

7. Circle which of the following is more acidic. Explain

8. Provide the reagents (at the arrows) for accomplishing the following transformations (in some cases more than one step may be necessary). The reagents should be in the correct order of sequence

9. Provide the product(s) of the following reactions. Show stereochemistry where appropriate.

10. Provide a mechanism for each of the following transformations. Proper use of curved and equilibrium arrows are required for full credit. Please show all steps and intermediates.

11. Provide the reagent(s), products and reactant(s) as indicated by the question mark(?)

continued:

12. Fill in the missing reagents a-d in the following synthetic scheme. Place your answer in the box provided..