Adversario, Trizia T.
2CHEM2 - CHM418L
1. If the theoretical yield of methylnitrobenzoate (C8H8NO4) is 2.00 g, what is the required initial weight
of methylbenzoate?
2.00 g C8H7O4 x (
1 mol C8H7NO4
)
181.04 g C8H7NO4
1 mol C8H8O2
)
1 mol C8H7NO4
x(
136.15 g C8H8O2
))
1 mol C8H8O2
x(
= 1.504087494 g C8H8O2
≈ 1.50 g C8H8O2
2. If the actual weight of methylnitrobenzoate is 1.47 g, what is the percent yield?
% yield = experimental yield theoretical yieldx 100
=1.472.00x 100
= 73.5%
Theoretical Yield
2.00 g
Weight of methyl
benzoate
(1) 1.50 g
(3.) Schematic Diagram of Recrystallization
Actual weight of MNB
Percent Yield
1.47 g
(2) 73.5%
(4) Mechanism Reaction
Synthesis of electrophile, NO2+
Nitration of methyl benzoate
(5) Type of chemical reaction: Electrophilic aromatic substitution
(6) Structure of product
(7) Identify the different protons with letters
(8-12) Match the following chemical shifts (ppm)
of the different protons: 4.001, 7.677, 8.378,
8.425, 8.862
(8) 3Ha
(9) 1Hb
(10) 1Hc
(11) 1Hd
(12) 1He
4.001
7.677
8.378
8.425
8.862
Singlet
Triplet
Doublet
Doublet
singlet
13. Characterize the substituted benzene as to activating or deactivating
For the nitration of methyl benzoate, the substituted benzene is deactivated (Substituent: Nitro Group,
NO2 – Deactivating)
a. What type of substituent is introduced in benzene by halogenation reaction?
Halogen (Cl or Br) – Deactivating
b. What type of substituent is introduced in benzene by Friedel-Crafts alkylation reaction?
Alkyl group (R) – Activating
c. What type of substituent is introduced in benzene by Friedel-Crafts acylation reaction?
Acyl group (RCO) - Deactivating