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Please determine the structures of compounds A through G, including stereochemistry where appropriate. (Hint: H:SOc: dehydration) „CH, (1) CH,Mgl (2) H,0* C,H,0 H,SO, H. P B heat |KMnO, TH,SO, heat warm, coned. C,H0 D (1) CH,Mgl (2) H,O" G heat C,H,Br PHCO,H C,H,O (1) Mg, ether (2) o HBr F E

Please determine the structures of compounds A through G, including stereochemistry where appropriate. (Hint: H:SOc: dehydration) „CH, (1) CH,Mgl (2) H,0* C,H,0 H,SO, H. P B heat |KMnO, TH,SO, heat warm, coned. C,H0 D (1) CH,Mgl (2) H,O" G heat C,H,Br PHCO,H C,H,O (1) Mg, ether (2) o HBr F E

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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
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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1. Please determine the structures of compounds A through G, including stereochemistry where appropriate. (Hint: H2SO4: dehydration) „CH, (1) CH,Mgl (2) H,0* C,H,0 H,SO, H,. P A В heat 1 KMnO, warm, coned. TH,SO, heat (1) CH,Mgl (2) H,0* CH16 C,H,0 D G TH,SO, heat C„H„0 C,H,Br C,H,0 (1) Mg. ether HBr PHCO,H F E (2) (3) H,O* 2. Please identify the reagents a through d in the following scheme: он CH3 CH3 CH3 OCH3 CH3 он CH3 он 3. What cleavage product would you expect from reaction of tetrahydrofuran with hot aqueous HI? tetrahydrofuran 4. Methyl phenyl ether can be cleaved to yield iodomethane and lithium phenoxide when heated with Lil. Please propose a mechanism for this reaction. (Hint: Lil is equal to Li* I and Li" is a Lewis acid.)
Transcribed Image Text:1. Please determine the structures of compounds A through G, including stereochemistry where appropriate. (Hint: H2SO4: dehydration) „CH, (1) CH,Mgl (2) H,0* C,H,0 H,SO, H,. P A В heat 1 KMnO, warm, coned. TH,SO, heat (1) CH,Mgl (2) H,0* CH16 C,H,0 D G TH,SO, heat C„H„0 C,H,Br C,H,0 (1) Mg. ether HBr PHCO,H F E (2) (3) H,O* 2. Please identify the reagents a through d in the following scheme: он CH3 CH3 CH3 OCH3 CH3 он CH3 он 3. What cleavage product would you expect from reaction of tetrahydrofuran with hot aqueous HI? tetrahydrofuran 4. Methyl phenyl ether can be cleaved to yield iodomethane and lithium phenoxide when heated with Lil. Please propose a mechanism for this reaction. (Hint: Lil is equal to Li* I and Li" is a Lewis acid.)
*CH3 methyl phenyl ether 5. Reduction of butan-2-one with NaBH4 yields butan-2-ol. Please explain why the product is chiral but not optically active. (Hint: R and s configuration) butan-2-one 6. tert-Butyl ethers can be prepared by the reaction of an alcohol with 2-methylpropene in the presence of an acid catalyst. Please propose a mechanism. H* R-OH + catalyst 2-methylpropene lert-butyl ethers 7. Epoxides react with Grignard reagents to yield alcohols. Please propose a mechanism. (Hint: Anti-addition) H H;C-MgBr HO then H;O" H, H 8. When 4-chlorobutane-1-thiol is treated with a strong base such as sodium hydride, NaH, tetrahydrothiophene is produced. Please suggest a mechanism for this reaction. (Hint: Sx2 mechanism) NaH CICH2CH2CH2CH2SH H2 + Nači Ether Tetrahydrothiophene
Transcribed Image Text:*CH3 methyl phenyl ether 5. Reduction of butan-2-one with NaBH4 yields butan-2-ol. Please explain why the product is chiral but not optically active. (Hint: R and s configuration) butan-2-one 6. tert-Butyl ethers can be prepared by the reaction of an alcohol with 2-methylpropene in the presence of an acid catalyst. Please propose a mechanism. H* R-OH + catalyst 2-methylpropene lert-butyl ethers 7. Epoxides react with Grignard reagents to yield alcohols. Please propose a mechanism. (Hint: Anti-addition) H H;C-MgBr HO then H;O" H, H 8. When 4-chlorobutane-1-thiol is treated with a strong base such as sodium hydride, NaH, tetrahydrothiophene is produced. Please suggest a mechanism for this reaction. (Hint: Sx2 mechanism) NaH CICH2CH2CH2CH2SH H2 + Nači Ether Tetrahydrothiophene
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