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Consider the following pairs of structures. Designate each chirality center as (R) or (S) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers.
 

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Consider the following pairs of structures. Designate each chirality center as (R) or (S) and identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers.
 

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Write appropriate structural formulas for (e) molecules with the formula C6H12 that contain no ring and that are diastereomers of each other.
 

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Write appropriate structural formulas for (d) molecules with the formula C6H12 that contain no ring and that are enantiomers of each other.
 

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Write appropriate structural formulas for (c) molecules with the formula C6H12 that contain one ring and that are diastereomers of each other.
 

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Write appropriate structural formulas for  (b) molecules with the formula C6H12 that contain one ring and that are enantiomers of each other. 
 

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Write appropriate structural formulas for (a) a cyclic molecule that is a constitutional isomer of cyclohexane. 
 

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Shown below are Newman projection formulas for (R,R)-, (S,S)-, and (R,S)-2,3-dichlorobutane.  (b) Which formula is a meso compound?

 

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Shown below are Newman projection formulas for (R,R)-, (S,S)-, and (R,S)-2,3-dichlorobutane. (a) Which is which?
 

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(a) Write the structure of 2,2-dichlorobicyclo[2.2.1]heptane. 
 

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Designate the (R) or (S ) configuration at each chirality center in the following molecules.
 

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Albuterol, shown here, is a commonly prescribed asthma medication. For either enantiomer of albuterol, draw a three-dimensional formula using dashes and wedges for bonds that are not in the plane of the paper. Choose a perspective that allows as many carbon atoms as possible to be in the plane of the paper, and show all unshared electron pairs and hydrogen atoms (except those on the methyl groups labeled Me). Specify the (R,S) configuration of the enantiomer you drew.
 

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(a) How many carbon atoms does an alkane (not a cycloalkane) need before it is capable of existing in enantiomeric forms? 
 

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Which of the following are chiral and, therefore, capable of existing as enantiomers? (a) 1,3-Dichlorobutane

 

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Compound C has infrared absorption in the 1620–1680-cm-1 and in the 3590–3650-cm-1 regions. Draw and label the (R) and (S) enantiomers of product C.
 

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Predict the structure of the product of this reaction:
The product has no infrared absorption in the 1620–1680-cm-1 region.
 

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(R)-(3-Chloro-2-methylpropyl) methyl ether (A) on reaction with azide ion (N 3-) in aqueous ethanol gives (S)-(3-azido-2-methylpropyl) methyl ether (B). Compound A has the structure ClCH2CH(CH3)CH2OCH3(a) Draw wedge–dashed wedge–line formulas of both A and B.
 

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When (S)-2-bromopropanoic acid [(S)-CH3CHBrCO2H] reacts with concentrated sodium hydroxide, the product formed (after acidification) is (R)-2-hydroxypropanoic acid [(R)-CH3CHOHCO2H, commonly known as (R)-lactic acid]. This is, of course, the normal stereochemical result for an SN2 reaction. However, when the same reaction is carried out with a low concentration of hydroxide ion in the presence of Ag2O (where Ag+ acts as a Lewis acid), it takes place with overall retention of configuration to produce (S)-2-hydroxypropanoic acid. The mechanism of this reaction involves a phenomenon called neighboring-group participation. Write a detailed mechanism for this reaction that accounts for the net retention of configuration when Ag+ and a low concentration of hydroxide are used.
 

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The reaction of chloroethane with water in the gas phase to produce ethanol and hydrogen chloride has ΔH° = +26.6 kJ mol -1 and ΔS° = +4.81 J K-1 mol-1 at 25°C. (d) In aqueous solution the equilibrium constant is very much larger than the one you just calculated. How can you account for this fact?
 

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The reaction of chloroethane with water in the gas phase to produce ethanol and hydrogen chloride has ΔH° = +26.6 kJ mol -1 and ΔS° = +4.81 J K-1 mol-1 at 25°C. (c) Calculate the equilibrium constant for the reaction.
 

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The reaction of chloroethane with water in the gas phase to produce ethanol and hydrogen chloride has ΔH° = +26.6 kJ mol -1 and ΔS° = +4.81 J K-1 mol-1 at 25°C. (b) Calculate ΔG° for the reaction. What can you now say about whether the reaction will proceed to completion?
 

 

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The reaction of chloroethane with water in the gas phase to produce ethanol and hydrogen chloride has ΔH° = +26.6 kJ mol -1 and ΔS° = +4.81 J K-1 mol-1 at 25°C.
(a) Which of these terms, if either, favors the reaction going to completion?
 

 

 

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In contrast to SN2 reactions, SN1 reactions show relatively little nucleophile selectivity. That is, when more than one nucleophile is present in the reaction medium, SN1 reactions show only a slight tendency to discriminate between weak nucleophiles and strong nucleophiles, whereas SN2 reactions show a marked tendency to discriminate. (b) Show how your answer accounts for the following:
 

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In contrast to SN2 reactions, SN1 reactions show relatively little nucleophile selectivity. That is, when more than one nucleophile is present in the reaction medium, SN1 reactions show only a slight tendency to discriminate between weak nucleophiles and strong nucleophiles, whereas SN2 reactions show a marked tendency to discriminate. (a) Provide an explanation for this behavior.
 

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Competition experiments are those in which two reactants at the same concentration (or one reactant with two reactive sites) compete for a reagent. Predict the major product resulting from each of the following competition experiments:
 

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