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This practice midterm covers key concepts in organic chemistry, focusing on reaction mechanisms and predicting products. It includes exercises on sn2 reactions, nucleophilic substitutions, elimination reactions, grignard reagents, and carbocation rearrangements. A valuable resource for students preparing for their organic chemistry midterm.
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B C N O F Ne
Ar
Kr
Xe
He H
Al Si P S Cl
Br
Li
Na
Rb
What products would you expect from the reaction of 1-bromopropane with each of the following?
a) NaNH 2
b) KOC(CH 3
3
c) NaI
d) NaCN
e) Mg, then H 2
Predict the product and give the stereochemistry (R or S, show work) resulting from
reaction of each of the following nucleophiles with (R)-2-bromobutane
a) CN
b) CH 3
2
c) CH 3
What products would you obtain from reaction of 1-pentanol with the following reagents?
a) SOCl 2
b) PBr 3
c) dry H 2
4
What Grignard reagent and what carbonyl compound might you start with to prepare the
following alcohols?
Grignard Carbonyl compound
a)
b)
3
3
Br
c)
When 4-chloro-1-butanol is trated with strong base such as sodium hydride, NaH,
tetrahydrofuran is produced. Suggest a mechanism. Show each of the intermediates and
show curved arrows to indicate the movement of electrons.
ClCH 2
2
2
2
NaH
Ether
2
NaCl