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Provide an explanation for the surprising fact that all-trans-1,2,3,4,5,6-hexaisopropylcyclohexane is a stable molecule in which all isopropyl groups are axial. (You may find it helpful to build a handheld molecular model.)
 

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Consider that cyclobutane exhibits a puckered geometry. Judge the relative stabilities of the 1,2-disubstituted cyclobutanes and of the 1,3-disubstituted cyclobutanes. (You may find it helpful to build handheld molecular models of representative compounds.)
 

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Which compound would you expect to be the more stable: cis-1,2-dimethylcyclopropane or trans-1,2-dimethylcyclopropane? Explain your answer.
 

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One compound whose molecular formula is C4H6 is a bicyclic compound. Another compound with the same formula has an infrared absorption at roughly 2250 cm-1 (the bicyclic compound does not). Draw structures for each of these two compounds and explain how the IR absorption allows them to be differentiated.
 

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Without referring to tables, decide which member of each of the following pairs would have the higher boiling point. Explain your answers. (e) Butane or CH3COCH3

 

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Without referring to tables, decide which member of each of the following pairs would have the higher boiling point. Explain your answers. (d) Butane or 1-propanol

 

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Without referring to tables, decide which member of each of the following pairs would have the higher boiling point. Explain your answers. (c) Propane or 2-chloropropane

 

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Without referring to tables, decide which member of each of the following pairs would have the higher boiling point. Explain your answers. (b) Heptane or pentane

 

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Without referring to tables, decide which member of each of the following pairs would have the higher boiling point. Explain your answers. (a) Pentane or 2-methylbutane
 

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Sketch curves similar to the one given in Fig. 4.8 showing the energy changes that arise from rotation about the C2 — C3 bond of (b) 2,2,3,3-tetramethylbutane. You need not concern yourself with actual numerical values of the energy changes, but you should label all maxima and minima with the appropriate conformations.
 

 

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Sketch curves similar to the one given in Fig. 4.8 showing the energy changes that arise from rotation about the C2 — C3 bond of (a) 2,3-dimethylbutane. You need not concern yourself with actual numerical values of the energy changes, but you should label all maxima and minima with the appropriate conformations.
 

 

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Write the structures of two chair conformations of 1- tert-butyl-1-methylcyclohexane. Which conformation is more stable? Explain your answer.
 

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Rank the following compounds in order of increasing stability based on relative ring strain.
 

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An alkane with the formula C6H14 can be prepared by hydrogenation of either of two precursor alkenes having the formula C6H12. Write the structure of this alkane, give its IUPAC name, and show the reactions.
 

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Four different cycloalkenes will all yield methylcyclopentane when subjected to catalytic hydrogenation. What are their structures? Show the reactions.
 

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Tell what is meant by an homologous series and illustrate your answer by writing structures for an homologous series of alkyl halides.
 

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A spiro ring junction is one where two rings that share no bonds originate from a single carbon atom. Alkanes containing such a ring junction are called spiranes.
(b) Write structures for other bicyclic molecules that fit this formula C7H12.
 

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A spiro ring junction is one where two rings that share no bonds originate from a single carbon atom. Alkanes containing such a ring junction are called spiranes.
(a) For the case of bicyclic spiranes of formula C 7H12, write structures for all possibilities where all carbons are incorporated into rings.
 

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Write structures for the following bicyclic alkanes: (b) Bicyclo[2.1.0]pentane

 

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Ignoring compounds with double bonds, write structural formulas and give names for all of the isomers with the formula C5H10.
 

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Write the structure(s) of the simplest alkane(s), i.e., one(s) with the fewest number of carbon atoms, wherein each possesses primary, secondary, tertiary, and quaternary carbon atoms. (A quaternary carbon is one that is bonded to four other carbon atoms.) Assign an IUPAC name to each structure.
 

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Write the structure and give the IUPAC systematic name of an alkane or cycloalkane with the formulas (c) C6H12 that has only primary and secondary hydrogen atoms.
 

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Write the structure and give the IUPAC systematic name of an alkane or cycloalkane with the formulas (b) C6H12 that has only secondary hydrogen atoms.
 

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Write the structure and give the IUPAC systematic name of an alkane or cycloalkane with the formulas (a) C8H18 that has only primary hydrogen atoms.
 

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The name sec-butyl alcohol defines a specific structure but the name sec-pentyl alcohol is ambiguous. Explain.
 

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