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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 33E

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Draw the major product or the starting material of the following reactions. Where
appropriate indicate if the product resulted from SN2, SN1, E2, or E1 in the box provided. When
a racemic mixture is formed, you must draw both enantiomers and write "racemic" in the box.
A)
NaCl
DMSO
B)
C)
Br
H₂O
NaOH
H₂O
E2
D)
NaOH
E)
F)
Cl
CH3OH
H₂O
E2
t-BuOK
E2

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The two pentene isomers react with mCPBA, followed by an aqueous workup with NaOH/H2Ó. Draw the key reaction intermediates and the product(s); use arrow pushing to explain the stereochemical outcomes of the reactions Intermediate Final Products MCPBA CO2OH mCPBA NaOH/H2O CI Intermediate Final Products MCPBA NaOH/H2O 6.
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draw the major product and state whether the relative stereochemistry of the added groups will be anti, syn or unknown
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Draw the products of these reactions clearly showing stereochemistry in each case if necessary. If the product is formed as a racemic mixture, clearly draw one stereoisomer with dash/wedge bonds and write “+en”. Circle whether each reaction occurs by an SN1 or SN2 pathway.
Which reaction mechanism will create a shift in the stereochemistry of the resulting product? a SN1 b SN2 c E1 d E2
Consider the E2 elimination of Compound A, and answer the following questions: (a) Label each stereocenter in Compound A with the correct R or S configuration. (b) Draw the structures of the major product with correct stereochemistry. Assume D and H have the same reactivity.
Draw the structure of the major product. If the answer for the product is a mixture of enantiomers draw one of the enantiomers and write "+ enantiomer." If the answer is a mixture of diaseteromers, draw all of them. Show arrow pushing mechanism and provide reasoning for each.

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