1 1)

2 2) 3)

3 Ag 2 O and NH 4 OH are the Tollens reagent 4) 5)

4 6) Draw sodium acetate. 7) Draw cycloheptanecarboxylic acid.

5 8) Draw 4-hexenal. 9) Draw 2,4-pentanedione.

6 10) Draw benzene-1,3-dicarboxaldehyde. 11) Draw the product(after workup) of 3-methyl-2-cyclohexenone with methyl Grignard.

7 12) Draw the product(after workup) of 3-methyl- 2-cyclohexenone with H 2./Pd-C. 13) Draw the keto tautomer of this enol.

8 14) Pentane-2,4-dione exists as a tautomeric mixture of 8% keto and 92% enol. Draw the enol form. The Z isomer is preferred due to the stabilization provided by hydrogen bonding.

9 15) 16)

10 17) 18)

11

12 19)

13

14 20)

a) Draw 3,3’-dimethylpentanoic acid. e) Draw m-hydroxybenzoic acid

a) b) c)

17 d) 19.33a) b)

18 c).

) In each group choose which compound is most acidic. Also choose which has the strongest conjugate base. a) Most acidic Strongest conjugate base b) Most acidic Strongest conjugate base

) No reaction

21 No reaction

) No reaction

23 No reaction

)

) No reaction

)

)

28

)

30

31 1)

32

33 2)

34 3)

35 4)

36 5)

37 6)

38 7)

39 8)

40 9)

41 10)

42 11)

43 12)

44 13)

45 14)

46 15)

47

) a) b)

49 c) d)

50 e) f)

51 g) h)

52 i) j)

53 k) l)

)

55

56

57