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A problem set for organic chemistry 2840-001, focusing on sn1 and sn2 reactions, identification of major organic products, and synthesis of organic compounds starting from 1methylcyclopentene. Students are required to write out the reactions and determine the stereochemistry of the products.
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Organic Chemistry 2840- Wheeler
Part 1 For the following transformations, identify the major organic product(s) for each and
decide if the process is SN1 or S (^) N2? Write NR for those reactions that provide little or no reaction product.
Product SN1 or S (^) N 2
Cl OH
Br
Cl Cl
1 eqv. H 2 O
OCH 3 NaOH, H 2 O
OCH 3 NaOH, H 2 O
OSO 2 Me
H 2 O, reflux
Br
NaOH, H 2 O
NaBr
Part 2 Show how you would synthesize the following organic compounds starting from 1-
methylcyclopentene? Pay close attention to stereochemistry.
Br
