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Organic Chemistry Reaction Mechanisms

The document provides a problem set with multiple chemistry problems involving reactions, naming compounds, reaction mechanisms, and synthesis proposals. The problem set covers topics such as predicting products, drawing reaction mechanisms, naming IUPAC compounds, and proposing syntheses.

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Bashir Ahmad
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9 views5 pages

Organic Chemistry Reaction Mechanisms

The document provides a problem set with multiple chemistry problems involving reactions, naming compounds, reaction mechanisms, and synthesis proposals. The problem set covers topics such as predicting products, drawing reaction mechanisms, naming IUPAC compounds, and proposing syntheses.

Uploaded by

Bashir Ahmad
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Problem Set #4

1) Predict the product(s) or provide reagents for the following reactions. For products, clearly
show stereochemistry. If the enantiomer also forms, write + E. MORE THAN ONE STEP MAY
BE REQUIRED. If more than one step, number individual steps.

a.

+
O

alkyl halide alkoxide

b.

NaH
Br OH

c.

CH3CH2 OH O

d.

OH O
e)

H3O+ (cat) O NH3


MeOH Et
CH3

f)

O 1. NaSPh
Me 2. H2O
D

g)
O
HO

OEt

h)

HO
OH +E

2) Name the following compounds with their IUPAC name

H
Br

O OH
3) 2-ethyl-2-methyloxirane is a chiral molecule. Hydrolysis of 2-ethyl-2-methyloxirane gives
another chiral molecule:

O hydrolysis OH
Et OH
Me
Me Et
2-ethyl-2-methyloxirane

a) Give a mechanism for the acid catalyzed hydrolysis of pure (R)-2-ethyl-2-methyloxirane


(treatment with H2O/H2SO4), showing the correct stereochemistry.

b) Give a mechanism for the treatment of pure (R)- 2-ethyl-2-methyloxirane with NaOH in water
(base-catalyzed hydrolysis), showing the correct stereochemistry

c) Do you get the same product for the acid catalyzed hydrolysis vs. the base catalyzed
hydrolysis? If not, explain why.

______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
4) Propose a synthesis for the following compounds

a)
O

additional building blocks


must contain no more than 3 carbons

b)
O O
OH +E
H
5) What are the two products formed from this reaction? Provide a detailed mechanism for the
formation of both products. Clearly show all charges and curvy arrows. Draw all relevant lone
pairs. Show the mechanism in a stepwise manner, DO NOT combine two steps into one.

HI (2 equiv)
O


Mechanism:

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