REVISED Propose structure C4H8O3

NMR

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

Convert 3-oxobutanoic acid into

Structure C7H14O2

Predict location of 18OO

18OR

R = Et

acidic water

R = tert Bu

acidic water

Propose Mechanism

Give synthesis

Give mechanism for reaction of dimethylamine and acetic anhydride

Give synthesis of 5-nonanone from 1-bromobutane

Obtain by aldol

convert

CHO

Give A, B, final product

Give mechanisms

Propose Mech

Fill in the details of the alternative synthetic paths

Ph

HBr

40 deg

?

Draw the occupied molecular orbital of benzene

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

azulenedipole moment 1.0Dnaphtalene

dipole moment = 0.0D

Why?

Sketch the occupied molecular orbitals for the pi system of benzene