REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

18
REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)
  • date post

    21-Dec-2015
  • Category

    Documents

  • view

    219
  • download

    3

Transcript of REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Page 1: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

REVISED Propose structure C4H8O3

NMR

2.62 (t,2H)3.38 (s, 3H)3.68 (t,2H)11.5 (s, 1H)

Page 2: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Convert 3-oxobutanoic acid into

Page 3: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Structure C7H14O2

Page 4: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Predict location of 18OO

18OR

R = Et

acidic water

R = tert Bu

acidic water

Page 5: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Propose Mechanism

Page 6: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Give synthesis

Page 7: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Give mechanism for reaction of dimethylamine and acetic anhydride

Give synthesis of 5-nonanone from 1-bromobutane

Page 8: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Obtain by aldol

Page 9: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

convert

CHO

Give A, B, final product

Page 10: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Give mechanisms

Page 11: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Propose Mech

Page 12: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Fill in the details of the alternative synthetic paths

Page 13: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Ph

HBr

40 deg

?

Page 14: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Draw the occupied molecular orbital of benzene

Is the C7H7 cation aromatic? Describe the energies of the orbitals. Draw resonance structures.

Page 15: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

azulenedipole moment 1.0Dnaphtalene

dipole moment = 0.0D

Why?

Page 16: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)

Sketch the occupied molecular orbitals for the pi system of benzene

Page 17: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)
Page 18: REVISED Propose structure C 4 H 8 O 3 NMR 2.62 (t,2H) 3.38 (s, 3H) 3.68 (t,2H) 11.5 (s, 1H)