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Which alkyl halide would you expect to react more rapidly by an S N2 mechanism? Explain your answer.
 

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Which alkyl halide would you expect to react more rapidly by an S N2 mechanism? Explain your answer.
 

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Write the two chair conformations of each of the following and in each part designate which conformation would be the more stable:

(d) cis-1-tert-butyl-4-methylcyclohexane.
 

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Write the two chair conformations of each of the following and in each part designate which conformation would be the more stable:  (c) trans-1-tert-butyl-4-methylcyclohexane,
 

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Write the two chair conformations of each of the following and in each part designate which conformation would be the more stable: (b) trans-1-tert-butyl-3-methylcyclohexane.
 

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Write the two chair conformations of each of the following and in each part designate which conformation would be the more stable: (a) cis-1-tert-butyl-3-methylcyclohexane.
 

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Write the structure and give the IUPAC systematic name of an alkane or cycloalkane with the formulas (d) C8H14 that has 12 secondary and 2 tertiary hydrogen atoms.

 

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Using the rules found in this chapter, give systematic names for the following or indicate that more rules need to be provided:
 

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Using the rules found in this chapter, give systematic names for the following or indicate that more rules need to be provided:
 

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Consider the cis and trans isomers of 1,3-di-tert-butylcyclohexane (build molecular models). What unusual feature accounts for the fact that one of these isomers apparently exists in a twist boat conformation rather than a chair conformation?
 

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Specify the missing compounds and/or reagents in each of the following syntheses: (c) Chemical reactions rarely yield products in such initially pure form that no trace can be found of the starting materials used to make them. What evidence in an IR spectrum of each of the crude (unpurified) products from the above reactions would indicate the presence of one of the organic reactants used to synthesize each target molecule? That is, predict one or two key IR absorptions for the reactants that would distinguish it/them from IR absorptions predicted for the product.
 

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Specify the missing compounds and/or reagents in each of the following syntheses:
 

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Specify the missing compounds and/or reagents in each of the following syntheses:
 

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trans-1,3-Dibromocyclobutane has a measurable dipole moment. Explain how this proves that the cyclobutane ring is not planar.
 

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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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