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Organic Reactions Problem Set 3

This document outlines Problem Set #3 for the Chemistry III course, focusing on organic reactions, due on April 23, 2025. It includes various tasks such as ranking compounds by reactivity, identifying acetals, drawing reaction mechanisms, and synthesizing compounds via the Wittig reaction. The document emphasizes academic integrity, group work guidelines, and penalties for late submissions.

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5 views4 pages

Organic Reactions Problem Set 3

This document outlines Problem Set #3 for the Chemistry III course, focusing on organic reactions, due on April 23, 2025. It includes various tasks such as ranking compounds by reactivity, identifying acetals, drawing reaction mechanisms, and synthesizing compounds via the Wittig reaction. The document emphasizes academic integrity, group work guidelines, and penalties for late submissions.

Uploaded by

lefurge1
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

CHEMISTRY III: Organic Reactions Spring 2025

Chem 2130

Problem Set #3
(19 pts)
Note: there are 24 pts available

DUE Wednesday April 23, 2025 by 4:00 pm

You may work with groups. The use of textbooks and notes is encouraged; however, discussion
of questions with anyone outside the class, including other faculty, will be considered academic
dishonesty. Failure to abide by these rules will at minimum result in a zero for the assignment.

**If you choose to work as a group on some or all the problems, please write the names of the
other students next to the problem or on the front. Remember that copying another student’s
answers or submitting other group members’ answers as your own without providing any
intellectual contribution is considered academic dishonesty.
.

*Late Penalty: Submission after the deadline is considered late. Late submissions will incur a
loss of 20% per day and will not be accepted after 2 days to ensure timely posting of answers.

Name(s):__________________________________________
1. Rank the following compounds in order of reactivity towards nucleophilic attack. (#1 = most
reactive); (0.5 pt)
O O O

H H H

2. Circle every acetal in the following compound. (0.5 pt)

O
O HO
O OH

O
MeO O

O
HO
OMe

3. Draw the mechanism for each of the following reactions. (8 pts)


a)
O [H+]
OH O O
HO

b)
O OH O
pyridine =
Cl pyridine O N
4. The following compound can be synthesized via a Wittig reaction. (3 pts)

a) Draw the possible carbonyl compounds and Wittig reagents needed to prepare this
compound.

b) Synthetically, which Wittig reagent would be easiest to prepare?

5. Write the appropriate reagents needed to complete each of the following transformations.
(4 pts)

O OH O
H Ph Ph
O

EtO

HO

6. Draw the major product for each of the following reactions. (8 pts)
a)
O
1. Et2CuLi

2. H3O+

b)
(2 equiv)
O (CH3)2NH

Cl
c)
O O
NH2
O

d)
SOCl2

OH
Ph
O
[H+], MeOH

e)
O NaOH, I2

Ph

f)
LDA, –78°C Br
O

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