CHM 201
Final Review Summary
*ATTENTION: it is the students’ responsible for all other topics than those on this review.
The format will be exactly the same as the first two exams. However, there will be more multiple choice questions
less of the short questions.
Multiple choice questions include
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Theories, short answers, nomenclature, stereochemistry etc…
All chapters (1-14, more will be on 1-8)
Predicting products and mechanisms
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SN1, SN2, E1, E2
Chapter 12.4, 14.5, 1.6
You are not responsible for any mechanisms in chapter 13-14
Reaction summary
Reduction of Aldehyde and Ketone
Catalytic hydrogenation
Lithium aluminum hydride
Grignard Reagent with aldehydes and ketones
Hemiacetal and Acetal Formation
Dang1
1.
Show the missing information for all the boxes (i.e starting materials, reagents and experimental
conditions) to synthesis each compound from 1-propanol. Right or wrong, no partial credit!!!
2.
Show all steps mechanisms for the following reaction. Don’t forget to use curved arrows to shoe the
movement of electrons in each step
Dang2
3.
Predict the product(s) for the following substitution reaction. Write a FULL and COMPLETE mechanism
for the product(s) you have predicted. Show complete arrow pushing and any intermediates. Only complete
mechanisms will be given full credit.
(3pts) Type of mechanism: ………………….
Grignard addition: preparation of alcohol
4.
Show a complete mechanism of how the below product is synthesize. (Note: there are two methods)
Dang3
5.
Addition of alcohol (ROH)  hemiacetal (w/1 mol Nu: )  acetal (2 mol Nu: )
Dang4