Kindly help me here. I have excluded some steps in my mechanism as I believe they are unnecessary. Help me decipher the major product and minor product and why. O1. Hg(OAc)2, H₂O/THF2. NaBH4, ethanolMethyl (E)-2-methylbut-2-enoate HgORH₂₂0-H30* ķOHOH0ORreductionbyNa BH u+ enantiomermajor producttvH₂0+ enantiomerTHo1

The question is based on the concepts of Organic reaction. we need to identify the product formed…

Answered: 1. Hg(OAc)2, H₂O/THF 2. NaBH4, ethanol…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Kindly help me here. I have excluded some steps in my mechanism as I believe they are unnecessary. Help me decipher the major product and minor product and why.

O
1. Hg(OAc)2, H₂O/THF
2. NaBH4, ethanol
Methyl (E)-2-methylbut-2-enoate

Hg
OR
H₂₂0
-H30* ķ
OH
OH
0
OR
reduction
by
Na BH u
+ enantiomer
major product
tv
H₂0
+ enantiomer
T
Ho
1

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Thank you for the answer. Kindly have a look at this textbook solution and explain wether it could be wrong or its something else.

Organic Chemistry Principles and Mechanisms 2e By Joel Karty - Copy.pdf - Adobe Acrobat Reader DC (32-bit)
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11.10 Kinetic versus
Thermodynamic
Control in
Electrophilic Addition
to a Conjugated
11.11 - Terpene
Biosynthesis:
Carbocation
Chemistry in Nature
12 - Electrophilic
Addition to Nonpolar
Bonds 2: Reactions
Involving Cyclic
Transition States
X
12.1 - Electrophilic
Addition via a
Three-Membered
Ring: The General
Mechanism
12.2 - Electrophilic
Addition of Carbenes:
Formation of
Solomon...
Organic ... x
617
Study_Gu...
(668 of 1587)
H₂O
HO
(a)
Methyl (E)-2-methylbut-2-enoate
ceeds through a more complex mechanism that is believed to involve free radicals
(species with unpaired electrons; see Chapter 25). Consequently, even though oxy-
mercuration takes place with anti addition, any stereochemistry of the C atom
bonded to Hg is scrambled during the reduction step, giving a mixture of both syn
and anti addition of water. This is exemplified in the oxymercuration-reduction of
methyl (E)-2-methylbut-2-enoate shown in Equation 12-24.
1. Hg(OAc)2, H₂O/THF
2. NaBH4, ethanol
?
Cambrid...
OH
Ou
Reduction with NaBH4 scrambles
the stereochemistry.
Syn addition
O
PROBLEM 12.12 Draw a detailed mechanism for each of the following reactions
and identify the major products.
H
+ Enantiomer
43% of product
(b)
Thermod...
1. Hg(OAc)2, H₂O/THF
2. NaBH4, ethanol
?
Anti addition
OH
O
+ Enantiomer
57% of product
Why does the addition of H₂O in Step 2 of Equation 12-23 follow Markovnikov's
rule? Like we saw with nucleophilic attack on a protonated epoxide or a bromonium
ion, the positive charge on Hg in the mercurinium ion is shared over the two C atoms
of the ring. The side of the ring that can handle the positive charge better will acquire
more of the charge and will more strongly draw in the nucleophile. In this case,
the side of the ring that has the secondary C atom acquires more of the positive
charge, not the side that has the primary C. Notice that the secondary C atom is the
CENG40...
Maungo...
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