CHEM 202 University of Illinois Organic Chemistry Hydrolysis Reactions Exam Acetals Be able to predict the product of acetal forming and hydrolyzing react

CHEM 202 University of Illinois Organic Chemistry Hydrolysis Reactions Exam Acetals

Be able to predict the product of acetal forming and hydrolyzing reactions
Be able to draw the mechanism for acetal formation
Use acetals as protecting groups in planning a synthesis
Imines and enamines
Be able to predict the product of imine and enamine forming and hydrolyzing reactions
Be able to draw the mechanism for imine and enamine formation
Reductive amination and amide reduction
Be able to predict the products of reductive amination and amide reduction reactions
Be able to draw the mechanism for the reduction part of a reductive amination
Be able to use reductive amination in planning a synthesis
Be able to use LiAlH4 in planning a synthesis
Wittig reaction
Recognize phosphonium ylide as a Wittig reagent
Be able to predict the products of a Wittig reactions
Be able to use the Wittig reaction in planning a synthesis Chem 202, Organic Chemistry I, Spring 2020
Mini–Exam #5
Name: ___________________________
This examination contains 5 questions worth a total of 50 points.
Answer all parts of all questions. There are Answer Pages at the back.
Write ALL your answers in the spaces provided on the answer page OR your own paper (using a
similar format on the answer pages. PLEASE: ONLY SCAN THE ANSWER PAGES/Your Own
Answer Sheets.
Time allowed: 4 hours total from download (Moodle) to submission on Gradescope. The exam
download and upload will be time-stamped.
A periodic table is included on the back page. This is an Open Book/Open Notes exam and
should be done on your own, NO discussion with other students, TA’s, mentors, etc. Do NOT
use the internet except for download and submission of the exam.
Good Luck – I know you are all working hard and can do it!
Honor Code: I pledge that I have adhered to the Mount Holyoke College Honor Code. I am
not aware of anyone else’s answers and I will not share the details of this examination with
anyone else.
1
1. (8 points) Predict the product of the following hydrolysis reactions.
(a)
a
b
(b)
O
O
NH
NH2
cat. p-TsOH
– H2O
cat. p-TsOH
– H2O
(c)
c
O
O
(d)
d
N
H3O+
H3O+
2. (8 points)
a. Using the Wittig reaction, Identify the necessary reagents to prepare the alkene
shown below.
b. The following undergoes an intramolecular Wittig reaction. Draw the product.
O
H
O
PPh3
3. (10 points) Design a synthesis for the following target molecule using the starting reagent
indicated and any other necessary reagents. A retrosynthesis is not required, but you may
find it helpful.
OH
O
O
H
N
2
4. (12 points) Fill in the missing intermediates and/or reagents from the scheme below.
a
b
CrO3/H2SO4
OH
c
O
N
H
H
NaBH3CN,
pH 4-5
cat. p-TsOH
– H2O
d
5. (12 points) Draw a complete mechanism for the following transformation.
HO
O
OH
p-TsOH
– H2O
O O
3
4

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