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

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

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter10: Oxidation And Reduction
Section: Chapter Questions
Problem 10CTQ
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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
Transcribed Image Text: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
Transcribed Image Text: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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Organic Chemistry Principles and Mechanisms 2e By Joel Karty - Copy.pdf - Adobe Acrobat Reader DC (32-bit) File Edit View Sign Window Help Home Tools Cambrid... D At least one signature is invalid. Bookmarks 凤 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... Signature Panel (12-24) ? Search 'Bates' T Export PDF Select PDF File Adobe Export PDF Convert PDF Files to Word Excel Online Convert to Sign In Microsoft Word (*.docx) Document Language: English (U.S.) Change Colect Fil Convert, edit and e-sign PDF forms & agreements Free 7-Day Trial
Transcribed Image Text:Organic Chemistry Principles and Mechanisms 2e By Joel Karty - Copy.pdf - Adobe Acrobat Reader DC (32-bit) File Edit View Sign Window Help Home Tools Cambrid... D At least one signature is invalid. Bookmarks 凤 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... Signature Panel (12-24) ? Search 'Bates' T Export PDF Select PDF File Adobe Export PDF Convert PDF Files to Word Excel Online Convert to Sign In Microsoft Word (*.docx) Document Language: English (U.S.) Change Colect Fil Convert, edit and e-sign PDF forms & agreements Free 7-Day Trial
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