What alcohols would give the following products on oxidation? (a) Он ÓH s od (b) (c) What products would you expect from the oxidation of the following compounds with (i) CrO3 in aqueous acid? (ii) with PCC? (a) tert-butanol (b) cyclohexanol (c) cyclohexanone What products would you expect from the oxidation of the following compounds with (i) KMNO4? (ii) with PCC? (a) HO он (b)

What alcohols would give the following products on oxidation? (a) Он ÓH s od (b) (c) What products would you expect from the oxidation of the following compounds with (i) CrO3 in aqueous acid? (ii) with PCC? (a) tert-butanol (b) cyclohexanol (c) cyclohexanone What products would you expect from the oxidation of the following compounds with (i) KMNO4? (ii) with PCC? (a) HO он (b)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.2: Preparing Ethers

Problem 2P: Why do you suppose only symmetrical ethers are prepared by the sulfuric-acid-catalyzed dehydration...

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Treatment of cis-4-bromocyclohexanol with HO− affords compound Aand cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and Bcontain different functional groups and are not isomers of each other.Propose structures for A and B and offer an explanation for theirformation.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout
Treatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4- bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
(a) How will you bring about the following conversions :(i) Ethanol to 3-hydroxybutanal (ii) Benzaldehyde to Benzophenone(b) An organic compound A has the molecular formula C8H16O2. It gets hydrolysed with dilute sulphuric acid and gives a carboxylic acid B and an alcohol C. Oxidation of C with chromic acid also produced B. C on dehydration reaction gives but-l-ene. Write equations for the reactions involved.
Mention and Write the following reaction mechanisms: a) thermal dehydration of 4-t-butylcyclohexanol with phosphoric acid as catalyst; b) addition of molecular bromine to the C= C double bond of 4-t- butylcyclohexene;
Why do you suppose only symmetrical ethers are prepared by the sulfuric-acid-catalyzed dehydration procedure? What product(s) would you expect if ethanol and 1-propanol were allowed to react together? In what ratio would the products be formed if the two alcohols were of equal reactivity?
Amines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (Ch3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
what products would expect to be produced in conce. HBr were reacted with 2,2- dimethyl-1-propanol? by what mechanism do you expect the major product to be produced. what products would be expected if 1- butanol were heated with concentrated sulfuric acid? by which mechanism would each product be formed. what products would be expected if (R)-2-butanol were heated with concenrated hydrobromic acid? if more than one product is expected what will be the major product?
1) (S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A (C4H8O). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B (C6H14O). Draw the structure of B. 2)
Deduce the structure of each compound from the information given. All unknowns in this problem have molecularformula C8H12.(a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC¬(CH2)6¬COOH. Draw the structure of W