Chem-224

Practice Exam-3 Dr. Chatterjee

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Followed by workup

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OH OH excess O
O
O
O O
O O
O
OH O O
HO O
OH pyridine O

O
O

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heat

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followed by heat

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Provide a complete, detailed mechanism with curved arrow formalism for the following reactions. Each
step must me explicitly written down, i.e. every attack of reagent, bond breaking and bond forming steps
must be shown!

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Devise a reasonable synthesis for the following compound from readily available
reagents and the starting material provided:

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Ph

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to

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to

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from cyclohexanone

from cyclohexanone

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from cyclohexanone

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to

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Histamine, an important chemical in our bodies, functions as a neurotransmitter and a potent vasodilator.
It is the agent that causes many symptoms of the common cold (hence antihistamin drugs being sold over
the counter). Explain and rank the basicity of each nitrogen in histamine:

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Provide the missing reagents for the transformations shown below.

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Provide a potential precursor to each of the following compounds (in other words, perform a
singlestep retrosynthesis). Also draw out the corresponding forward reaction with reagent that
could be used to synthesize the given molecule. Note: In many cases, there is more than one
correct solution
a.

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Provide detailed arrow-pushing mechanisms for the following transformations.

h.

i)

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1. Sn / HCl
NO 2 followed by NaOH HNO3, H2SO 4

O
2.
Cl
N

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Provide the necessary reagents for the following transformations. More than one step may be
required.

Draw a detailed mechanism for the reaction below

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Provide syntheses of the following target molecules. You may use common reagents, fragments
of 2-carbons or less (these fragments may contain atoms other than just carbon, including
hydrogen, oxygen, MgBr, and Li), and any of the compounds shown in the Toolbox. It is not
necessary to show mechanisms or a retrosynthetic analysis in your solution.

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Provide synthesis for the following conversions:

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Propose a detailed stepwise mechanism for the reactions shown below. Use curved arrows to show
moment of electrons and Include all intermediates where appropriate.

a.

O
O O
HO OH

pTsOH , heat

MeO
Dean Stark removal of H2O
MeO

b.

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c.

d.

e.

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f.

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Propose a synthesis for the following molecule

Complete the following reaction sequence.

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Complete the following reaction sequence.

Draw the hydrolysis products formed when Frontalin is treated with aqueous acid

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Provide the detailed stepwise mechanism to convert benzoic acid to ethylbenzoate.

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Predict the trend in acidity for the following substituted phenols. Rank by increasing acidity and explain.

a) Predict the trend in acidity for the following substituted carbonyl compounds. Rank by
increasing acidity and explain the origin of this difference:

b) Rank the hydrogens shown in bold in the following compound by increasing acidity and
explain the origin of this difference:

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Cyclopentadienone is unstable and cannot be isolated. It furnishes a Diels-Alder adduct. However,

Cycloheptatrienone is stable and has been synthesized. Comment on the difference in behavior of the 2
ketones.

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The major aromatic product of the following reaction is:

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