Practice Final KEY

Chem-252 Practice Final Dr.
Chatterjee
Please review previous practice exams for spectroscopy and reactions that were covered in
exam 1 and 2. This practice is for the new material.
Chem-252 Practice Final Dr. Chatterjee
Provide the necessary reagents for the following transformations. More than one step may be
required.
Draw a detailed mechanism for the reaction below

The mass spectrum of the compound shown below shows two distinctive peaks that are typical of a
fragmentation of a carboxylic acid. Draw the structure of the fragments.
Provide the missing reagents for the transformations shown below.

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:
c. Devise a reasonable synthesis for the following compound from readily available
reagents and the starting material provided:
Provide a potential precursor to each of the following compounds (in other words,
perform a single step 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
[Part a has been done for you as an example; mastering problem 3 will help you
with the synthesis/retrosynthesis problems]
a.
Provide detailed arrow-pushing mechanisms for the following transformations.
h.
i)
h.
i)
--------------------------------------------------------------------------------------------------------------
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.
6. Provide structures of the

products obtained from nucleophilic aromatic substitution and briefly explain why the reaction gives
two products instead of one (substitution reaction)
7. Provide synthesis for the following conversions:

a.
b.
c.
d.
e.
f.
Propose a synthesis for the following molecule
------------------------------------------------------------------------------------------------------------------------------------------
11. Complete the following reaction sequence.

Complete the following reaction sequence.
Draw the hydrolysis products formed when Frontalin is treated with aqueous acid
Provide the detailed stepwise mechanism to convert benzoic acid to ethylbenzoate.

Predict the trend in acidity for the following substituted phenols. Rank by increasing acidity and explain.
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:
Hckels rule predicts that for a monocyclic compound to be aromatic there must be a fully conjugated
system containing (4n + 2) electrons. The correct answer is choice (C); two electrons are provided
by each of the double bonds giving a total of 6, satisfying 4n + 2 when n = 1. The unshared electron pair
on nitrogen is perpendicular to
the cloud, and does not count in determining aromaticity. Choice (A) is incorrect because there are 8
electrons and the compound is not aromatic. When nitrogen is bonded as in choice (A), the unshared
electron pair is parallel to the system and counts
toward determining aromaticity. Choice (B) is incorrect because it is not fully conjugated; there is a CH 2
group in the ring. Cyclic conjugation is necessary for a compound to be aromatic. Choice (D) is incorrect
because, even though it is aromatic, it
is not a heterocycle. The heteroatom (nitrogen in this problem) must be one of the atoms
of the ring for a compound to be a heterocycle.
The major aromatic product of the following reaction is:

The major aromatic product of the following reaction is:
The reaction is an example of Friedel-Crafts acylation, using acetic anhydride [(CH3CO)2O] as the
acylating agent. The product is a methyl ketone. Additionally, you
need to remember that chlorine is an ortho, para directing group so the correct answer is
choice (A). Choice (B) is incorrect because the ketone group is meta to the chlorine.
Choices (C) and (D) are incorrect because they are both esters and are not formed in
Friedel-Crafts reactions.

Practice Final KEY

Hochgeladen von

Dokumentinformationen

Originaltitel

Copyright

Verfügbare Formate

Dieses Dokument teilen

Dokument teilen oder einbetten

Freigabeoptionen

Stufen Sie dieses Dokument als nützlich ein?

Sind diese Inhalte unangemessen?

Copyright:

Verfügbare Formate

Practice Final KEY

Hochgeladen von

Copyright:

Verfügbare Formate

Chem-252 Practice Final Dr.

Draw a detailed mechanism for the reaction below

Provide the missing reagents for the transformations shown below.

Provide detailed arrow-pushing mechanisms for the following transformations.

6. Provide structures of the

7. Provide synthesis for the following conversions:

Propose a synthesis for the following molecule

11. Complete the following reaction sequence.

Complete the following reaction sequence.

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

of the ring for a compound to be a heterocycle.

The major aromatic product of the following reaction is:

The major aromatic product of the following reaction is:

Das könnte Ihnen auch gefallen