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Write a structural formula for the most stable conformation of each of the following compounds: 

(b)  2,2,5,5-Tetramethylhexane (zigzag conformation of entire molecule) 

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Write a structural formula for the most stable conformation of each of the following compounds: 

(a)  2,2,5,5-Tetramethylhexane (Newman projection of conformation about C-3—C-4 bond) 

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Ambroxol is a drug used to treat bronchopulmonary disease. Draw the structure of ambroxol in the alternative chair conformation. Which of the two conformations is more stable? 

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 (c) How many alkenes yield methylcyclobutane? 

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In each of the following groups of compounds, identify the one with the largest heat of combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability? 

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In each of the following groups of compounds, identify the one with the largest heat of combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability? 

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In each of the following groups of compounds, identify the one with the largest heat of combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability? 

(b)  cis-1,2-Dimethylcyclopentane, methylcyclohexane, 1,1,2,2-tetramethylcyclopropane 

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In each of the following groups of compounds, identify the one with the largest heat of combustion and the one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative stability? 

(a)  Cyclopropane, cyclobutane, cyclopentane 

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Excluding compounds that contain methyl or ethyl groups, write structural formulas for all the bicyclic isomers of

(b) C6H10

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Excluding compounds that contain methyl or ethyl groups, write structural formulas for all the bicyclic isomers of (a) C5H8 

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Select the compounds in each group that are isomers and specify whether they are constitutional isomers or stereoisomers. 

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Select the compounds in each group that are isomers and specify whether they are constitutional isomers or stereoisomers. 

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Select the compounds in each group that are isomers and specify whether they are constitutional isomers or stereoisomers. 

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Select the compounds in each group that are isomers and specify whether they are constitutional isomers or stereoisomers. 

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Select the compounds in each group that are isomers and specify whether they are constitutional isomers or stereoisomers. 

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Determine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds. 

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(b) How many alkene(s) are possible to yield 2,3-dimethylbutane by hydgrogenation. Draw the structure(s)? 

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Determine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds. 

(d) cis-1,2-Dimethylcyclopentane and trans-1,3-dimethylcyclopentane 

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Determine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds. 

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(a) How many alkenes yield 2,2,3,4,4-pentamethylpentane on catalytic hydrogenation? 

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Determine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds. 

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Which do you expect to be the more stable conformation of cis-1,3-dimethylcyclobutane, A or B? Why?

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Even though the methyl group occupies an equatorial site, the conformation shown is not the most stable one for methylcyclohexane. Explain. 

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Identify all atoms that are (a) anti and (b) gauche to bromine in the conformation shown for CH3CH2CH2Br. 

 

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Sketch an approximate potential energy diagram for rotation about the carbon–carbon bond in 2,2-dimethylpropane similar to that shown in Figures 3.4 and 3.7. Does the form of the potential energy curve of 2,2-dimethylpropane more closely resemble that of ethane or that of butane? 

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