ORGANIC CHEMISTRY(LL)-W/ACCESS >CUSTOM<
10th Edition
ISBN: 9781259917196
Author: Carey
Publisher: MCG CUSTOM
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Chapter 6, Problem 29P
If the temperature is not kept below
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The p-toluenesulfonate derived from (R)-2-octanol and p-toluenesulfonyl chloride was allowed to react with sodium benzenethiolate (C6H5SNa). Give the structure, including stereochemistry and the appropriate R or S descriptor, of the product.
A racemic mixture of 2-methyl-1-phenyl-1-butanone is formed when (R)-2-methyl-1-phenyl-1-butanone is dissolved in an acidic or basic aqueoussolution. Give an example of another ketone that undergoes acid- or base-catalyzed racemization.
we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?
Chapter 6 Solutions
ORGANIC CHEMISTRY(LL)-W/ACCESS >CUSTOM<
Ch. 6.1 - Prob. 1PCh. 6.2 - 1-Bromo-3-chloropropane reacts with one molar...Ch. 6.3 - Prob. 3PCh. 6.3 - The Fischer projection for (+)-2-bromooctane is...Ch. 6.3 - Would you expect the 2-octanol formed by SN2...Ch. 6.3 - Prob. 6PCh. 6.4 - Prob. 7PCh. 6.4 - The first step in the synthesis of the...Ch. 6.6 - Prob. 9PCh. 6.6 - Prob. 10P
Ch. 6.7 - Prob. 11PCh. 6.8 - Prob. 12PCh. 6.9 - Diethyl ether (CH3CH2OCH2CH3) has a dielectric...Ch. 6.9 - Unlike protic solvent which solvate from complexes...Ch. 6.10 - Prob. 15PCh. 6.10 - Prob. 16PCh. 6.10 - The hydrolysis of sulfonate of 2-octanol is...Ch. 6.11 - Prob. 18PCh. 6 - Prob. 19PCh. 6 - Prob. 20PCh. 6 - Both of the following reactions involve...Ch. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Sodium nitrite (NaNO2) reacted with 2-iodooctane...Ch. 6 - Prob. 25PCh. 6 - Prob. 26PCh. 6 - Prob. 27PCh. 6 - The reaction of 2,2-dimethyl-1-propanol with HBr...Ch. 6 - If the temperature is not kept below 25oC during...Ch. 6 - The reaction of cyclopentyl bromide with sodium...Ch. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Write an equation, clearly showing the...Ch. 6 - Prob. 34PCh. 6 - Based on what we know about nucleophiles and...Ch. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41DSPCh. 6 - Prob. 42DSPCh. 6 - Prob. 43DSPCh. 6 - Prob. 44DSPCh. 6 - Prob. 45DSPCh. 6 - Prob. 46DSP
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- When a primary alcohol is treated with p-toluenesulfonyl chloride at room temperature in the presence of an organic base such as pyridine, a tosylate is formed. When the same reaction is carried out at higher temperature, an alkyl chloride is often formed. Explain.arrow_forwardGive a plausible mechanism for the reaction of o-bromobenzoic acid and 1-propanol (with HCI) to yield propyl o-bromobenzoate.arrow_forwardWhen warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forward
- -Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardOutline a mechanism for the dehydration of 4-methylcyclohexanol catalyzed by phosphoric acid.arrow_forwardCompelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.arrow_forward
- Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous−OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.arrow_forwardIf in the Grignard synthesis of benzoic acid a student determined that his crude product was a mixture of benzoic acid and bromobenzene, map out a series of extractions using the following solvents and solutions to get pure benzene or its salt in an ether solution. Methyl tert-butyl ether (MTBE) 3M HCl 3M NaOHarrow_forwardGiven this retrosynthetic analysis, propose a synthesis for labetalol from salicylic acid and benzyl chloride. [Note: The conversion of salicylic acid to (E) involves a Friedel-Crafts acylation in which the phenolic -OH must be protected by treatment with acetic anhydride to prevent the acylation of the -OH group. The protecting group is later removed by treatment with KOH followed by acidification.]arrow_forward
- The reaction of sodium borohydride with ketones proceeds rapidly at room temperature, forming an intermediate borate ester which is hydrolyzed to give the product alcohol: 4 R2C=O + Na+BH4- ---> (R2CHO)4B-Na+ (R2CHO)4B-Na+ + 2H2O ---> 4R2CHOH + Na+BO2- Rewrite these two steps using benzil as the ketone, and using structural formulas throughout, rather than the condensed forms above.arrow_forwardThe reaction of sodium borohydride with ketones proceeds rapidly at room temperature, forming an intermediate borate ester which is hydrolyzed to give the product alcohol: 4 R2C=O + Na+BH4- ---> (R2CHO)4B-Na+ 2. (R2CHO)4B-Na+ + 2H2O ---> 4R2CHOH + Na+BO2- Rewrite these two steps using benzil as the ketone, and using structural formulas throughout, rather than the condensed forms above. For example, the structural formula for water is H-O-H. Please write them by hand and paste them in.arrow_forwardElectrophilic nitration of benzoic acid gives almost exclusively 3-nitrobenzoic acid. By drawing the appropriate resonance forms of the intermediate cations resulting from attack of [NO2]+, explain this result.arrow_forward
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