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- 2-Methoxy-2-methylpropane on heating with HBr gives : (A Methoxymethane and Propylbromide (B Methanol and 2-Bromo-2-methylpropane 2-Methylpropan-2-ol and Bromomethane 2-Methylpropan-1-ol and bromomethaneWhen 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.-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
- 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.A key step in the synthesis of naproxen, an NSAID more commonly known by its brand name, Aleve (Section 3.9), is a coupling reaction of 2-bromo-6-methoxynaphthalene to form 2-methoxy-6-vinylnaphthalene. Show three different coupling reactions, and the required reagents, that could be used tocarry out this step.Treatment of compound A (C8H17Br) with NaOCH2CH3 affords twoconstitutional isomers B and C. Ozonolysis of B affords CH2=O and(CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 andCH3CH2CHO. What is the structure of A?
- [18] Which of following compound will undergo solvolysis with methanol to yield the two shown? H3C OCH3 CH3 OCH3 (a) (15,3S)-1-bromo-1,3-dimethyl-cyclohexane (b) (1R,3R)-1-bromo-1,3-dimethyl-cyclohexane (c) (15,3R)-1-bromo-1,3-dimethyl-cyclohexane (A) (1R)-1-bromo-1,3-dimethyl-cyclohexane (e) (15)-1-bromo-1,3-dimethyl-cyclohexane19.24 Cyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. O Os04 H₂O₂ C6H12O₂ HIO, CH1002 base CHO 1-Cyclopentenecarbaldehyde Propose a structural formula for each intermediate compound.A key step in the synthesis of naproxen, an NSAID more commonly known by its brand name, Aleve (Section 3.9), is a coupling reaction of 2-bromo6-methoxynaphthalene to form 2-methoxy-6-vinylnaphthalene. Show three different coupling reactions, and the required reagents, that could be used to carry out this step.
- Draw structural formulas for the isomeric carbocation intermediates formed on treat- ment of each alkene with HCl. Label each carbocation 1°, 2°, or 3° and state which of the isomeric carbocations forms more readily. CH₂CH3 (a) H₂C=C (c) CH3 CH3 (b) (d) H₂C-CH=CH-CH3Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H₂O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data? a. Isomer A is cyclopentene and isomer is 1-pentyne O b. Isomer A is cyclopentene and isomer B is 1-methylcyclobutene c. Isomer A is cyclopentene and isomer B is 3-methylcyclobutene d. Isomer A is 1-methylcyclobutene and isomer B is 3-methylcyclobuteneTwo isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?