(a)
To determine: The mechanism of the given reaction that accounts for racemisation with excess inversion.
Interpretation: The mechanism of the given reaction that accounts for racemisation with excess inversion is to be stated.
Concept introduction: The reaction between
(b)
To determine: The mechanism of the given reaction that accounts for complete retention of configuration.
Interpretation: The mechanism of the given reaction that accounts for complete retention of configuration is to be stated.
Concept introduction: The reaction between
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Chapter 11 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
- - How could the following changes in reaction conditions affect the rate of the reaction when isopropanol (IPA) reacts with 2-bromo-2-methylpentane? The concentration of the IPA is halved by adding petroleum ether as the solvent. b. The concentration of the bromoalkene is quadrupled. а.arrow_forward1. When cyclopentene is allowed to react with bromine in an aqueous solution of sodium chloride, the products of the reaction are trans-1,2-dibromocyclopentane, trans-1-bromo-2-chlorocyclopentane, and trans-2-bromo-1-cyclopentanol. Write mechanisms to account for the formation of all these products.arrow_forward4.) Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule: hydrolysis CH, H,C он HO a. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H;SO, H,O), showing the correct stereochemistry.arrow_forward
- 3. Completely explain the following observation: Br Br2 Br₂ Br Br + HBr A. Both reactions involve two bromine atoms adding across a double bond B. Both reactions involve a neutral intermediate with a single bromine atom C. After addition to benzene, elimination is favourable to regain aromaticity D. After addition to cyclohexene, the addition of a second bromine atom is favourablearrow_forward1) a. Propose a mechanism to account for the following reaction: 1-methylcyclohex-2-enol reacts with HI to give 3-iodo-3-methylcyclohex-1-ene and 3-iodo-1-methylcyclohex-1-ene. b. When 1-(1-methylethyl)cyclohexene (1-isopropylcyclohexene) is treated with a solution of HBr in Et₂0 2-bromo-2-cyclohexylpropane is the resulting product. Write the reaction and propose a mechanism using curved arrows to indicate the electron flow in each step c. Draw a mechanism that accounts for the following transformation. HO. LOCH3 com OCH3 CF3CO₂Harrow_forward1) a. Propose a mechanism to account for the following reaction: 1-methylcyclohex-2-enol reacts with HI to give 3-iodo-3-methylcyclohex-1-ene and 3-iodo-1-methylcyclohex-1-ene. b. When 1-(1-methylethyl)cyclohexene (1-isopropylcyclohexene) is treated with a solution of HBr in Et₂O 2-bromo-2-cyclohexylpropane is the resulting product. Write the reaction and propose a mechanism using curved arrows to indicate the electron flow in each step. c. Draw a mechanism that accounts for the following transformation. НО. LOCH3 OCH 3 CF3CO₂Harrow_forward
- Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forwardai. Reaction of the same 1-butene with cold KMnO4/ -OH gives compound ‘C’. Identify compound C. ii. Reaction of 1- butene with Hot KMnO4/-OH gives compound ‘D’ followed by acidification of the mixture to give compound ‘E’. Identify compounds D and E. iii. When 1- butene is treated with HBr in the presence of a peroxide, give the name and structure of the product formed. b. Dehydrohalogenation of alkylhalides always gives more than one product. Using 3, methyl 2-butyl chloride, explain this observation.arrow_forwardThe reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion thanretention of configuration. Propose a mechanism that accounts for racemization with excess inversion.(b) Under the same conditions, an optically active sample of trans-2-bromocyclopentanol reacts with concentrated aqueous HBr to give an optically inactive product, (racemic) trans-1,2-dibromocyclopentane. Proposea mechanism to show how this reaction goes with apparently complete retention of configuration, yet withracemization. (Hint: Draw out the mechanism of the reaction of cyclopentene with Br2 in water to give thestarting material, trans-2- bromocyclopentanol. Consider how parts of this mechanism might be involved in thereaction with HBr.)arrow_forward
- 8. Suggest a detailed step-by-step reaction mechanism for the reactions shown in a-b (use arrows to show electron flow). CH3 H3C CH3 (a) HO. ОН H,SO4 CH3 CH3 CH3OH CH3 (b) CH-I + HI OCH3arrow_forwardPropylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule. A. Provide a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide (treatment with H2SO4/H2O), showing the correct stereochemistry. B. Provide a mechanism for the treatment of pure (R)-propylene oxide with NaOH in water (base-catalyzed hydrolysis), showing the correct stereochemistry. C. Explain why acid-catalyzed hydrolysis of optically active propylene oxide gives a product with a rotation in the opposite direction from the product of the base catalyzed hydrolysis.arrow_forward3. For each of the reactions below, redraw the alkyl halide with the correct stereochemistry as indicated and provide mechanisms with explanations to account for the products observed. OCH, a. CH,OH R-enantiomer Racemic mixture b. NaCN H3C-Ç-CH2CH3 H3C-C-CH2CH3 Acetone CN Br R-enantiomer S-enantiomcr HIC HICarrow_forward
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