CHEM 2420 University of Pittsburgh Organic Chemistry Spectroscopy Worksheet

CHEM2420 Organic Chemistry Chap 9.2 Aromatic Substitution Reactions WorksheetName:_______________________
(16 points)
Starting with benzene as your only source of aromatic compounds, how would you synthesize the following
substances? Assume that you can separate ortho and para isomers if necessary.
p-Chlorotoluene
m-Bromonitrobenzene
o-Bromobenzenesulfonic acid
m-Chlorobenzenesulfonic acid
Starting with either benzene, phenol, or toluene, how would you synthesize the following substances? Assume
that ortho and para isomers can be separated
2-Bromo-4-methylphenol
1,3,5-Trinitrobenzene
2,4,6-Tribromoaniline
2-Chloro-4-nitrotoluene
CHEM2420 Organic Chemistry Chap 9.3 Aromatic Substitution Reactions Worksheet
Name:_______________________
(12 points)
Explain why these compounds react more slowly than benzene in electrophilic aromatic substitution reactions
and give predominantly meta products: (6 points)
CF3
+N(CH ) Cl3 3
(6 points) In the empty spaces below, show the steps necessary for the following transformations (include all
reagents). Remember to pay attention to directing effects when you plan your synthesis. Note in some cases it
may be impossible to avoid getting mixtures of isomeric products; if this is the case please indicate it.
Organic Chem 2: Spectroscopy
Worksheet # 10.1
(8 points)
Interpretation of Mass Spectrometer Data
Name: ________________________
Due Date: _____________
The spectrum below is the MS data for an ether compound with the formula C4H10O.
Answer the questions that follow the spectrum.
1. Identify the parent peak. _______________
2. Identify the base peak. ______________
3. Give likely structures for the fragments at m/z = 59, 45, 31