Problem Set I
Dimethylformamide (DMF) is a common solvent in organic synthesis with formula
HCON(CH3)2. Draw resonable resonance structures. Include resonance arrows,
electron pushing arrows, non-bonding electrons and charges.
Problem Set II
Use line structures to draw all the ALKENE isomers with the formula C5H10 and name
2. Rank the isomers in order of increasing stability.
3. How many signals do you expect in the 1H NMR spectra for each of the is
Problem Set III
1. The six isomers of dimethylcyclobutane are shown below. Answer the questions assuming
that the cyclobutane ring is planar.
Draw the mirror image of the six isomers using the dotted line as mirror and determine
1. Trans-1,2 dimethyl cyclohexane has two enantiomers, each enantiomer has two chair
conformations and each chair can be drawn from three different perspectives.
Label the structures as A or B based on their configuration
1. Write down the reaction and detailed mechanism to convert allyl bromide into one of
the structural isomers of bromopropanol. Dont forget all the appropriate reagents,
arrows, free electron pairs and charges.
2. Does the pr
Problem Set VI
1. Classify the following statements as SN1, SN2, E1 or E1 reactions. More than one could
apply in each case.
Concerted transition state
Reaction rate = k [R-L][Nu]
Mechanism is viable only in polar
Problem Set VIII
1. There are two possible routes to synthesize propyl isopropyl ether (F+G or B+E). Write
the missing reagents on the arrows and the missing structures in the squares. Hint:
Williamson ether synthesis.