Chapter 4 Isomers: The Arrangement of Atoms in Space
1) What type of isomers are CH 3 CH 2 OCH 3 and CH 3 CH 2 CH 2 OH? A) constitutional B) symmetrical C) configurational D) conformational ) stereochemical Ans!er" A #ection" $%1 2) What is the relationship &et!een the follo!ing compounds? A) configurational isomers B) conformational isomers C) constitutional isomers D) structural isomers ) positional isomers Ans!er" A #ection" $%1 3) What is the relationship &et!een the follo!ing compounds? A) constitutional isomers B) enantiomers C) diastereomers D) conformational isomers ) superimposa&le !ithout &ond rotation Ans!er" A #ection" $%1 1 Copyright ' 2(1$ )earson ducation* +nc, $) What is the relationship &et!een the structures sho!n &elo!? A) not isomers B) constitutional isomers C) conformational isomers D) configurational isomers ) enantiomers Ans!er" B #ection" $%1 -) What is the relationship &et!een the structures sho!n &elo!? A) diastereomers B) constitutional isomers C) conformational isomers D) configurational isomers ) enantiomers Ans!er" B #ection" $%1 .) +dentify the pair of compounds, A) identical B) conformation isomers C) constitutional isomers D) configurational isomers ) none of the a&o/e Ans!er" D #ection" $%1 2 Copyright ' 2(1$ )earson ducation* +nc, 0) Which of the follo!ing cannot e1hi&it chirality? A) 2* 3%di&romo&utane B) 1* 3%di&romo&utane C) 1* 2%dichloro&utane D) 1* $%di&romo&utane ) 1%&romo%2%chloro&utane Ans!er" D #ection" $%2 3 Copyright ' 2(1$ )earson ducation* +nc, 2) Which of the follo!ing compounds is chiral? A) B) C) D) ) Ans!er" B #ection" $%2 $ Copyright ' 2(1$ )earson ducation* +nc, 3) +s the molecule sho!n &elo! chiral or achiral? Ans!er" achiral #ection" $%2 1() +s the molecule sho!n &elo! chiral or achiral? Ans!er" chiral #ection" $%2 11) +s the molecule sho!n &elo! chiral or achiral? Ans!er" achiral #ection" $%2 12) +s the molecule sho!n &elo! chiral or achiral? Ans!er" achiral #ection" $%2 - Copyright ' 2(1$ )earson ducation* +nc, 13) +dentify the compounds that are not chiral, Ans!er" A* B* and D #ection" $%2 1$) Which of the follo!ing compounds has an asymmetric center? A) + B) ++ C) +++ D) +4 ) 4 Ans!er" C #ection" $%3 1-) Ho! many asymmetric centers are present in a molecule of 2*$*.%trimethylheptane? A) ( B) 1 C) 2 D) 3 ) $ Ans!er" A #ection" $%3 . Copyright ' 2(1$ )earson ducation* +nc, 1.) Ho! many asymmetric centers are present in the compound sho!n &elo!? A) 1 B) 2 C) 3 D) $ ) - Ans!er" C #ection" $%3 10) Ho! many asymmetric centers are present in the compound &elo!? Ans!er" - #ection" $%3 12) +dentify the pair of compounds, A) identical B) conformational isomers C) constitutional isomers D) configurational isomers ) none of the a&o/e Ans!er" D #ection" $%3 0 Copyright ' 2(1$ )earson ducation* +nc, 13) 5i/e the num&er of asymmetric centers in limonene, A) 2 B) 3 C) 1 D) - ) $ Ans!er" C #ection" $%3 2() +dentify the compound6s) !ith asymmetric centers, A) B) C) D) ) Ans!er" C #ection" $%3 2 Copyright ' 2(1$ )earson ducation* +nc, 21) A and B are stereoisomers, 7hey are nonsuperimposa&le and are mirror images of one another, Which of the follo!ing &est descri&es the relationship &et!een A and B? A) structural isomers B) enantiomers C) conformational isomers D) diastereomers ) constitutional isomers Ans!er" B #ection" $%$ 22) What is the relationship &et!een the structures sho!n &elo!? A) enantiomers B) diastereomers C) configurational isomers D) identical compounds ) constitutional isomers Ans!er" D #ection" $%$ 3 Copyright ' 2(1$ )earson ducation* +nc, 23) Which of the follo!ing compounds is an enantiomer of the structure &elo!? A) B) C) D) A and B ) +t does not ha/e an enantiomer, Ans!er" #ection" $%$ 2$) Which of the follo!ing statements correctly descri&es the molecule sho!n &elo!? A) +t is achiral, B) +t is meso, C) +ts asymmetric center possesses the R configuration, D) 7he mirror image of this molecule is its enantiomer, ) 7he molecule possesses enantiotopic hydrogens, Ans!er" D #ection" $%$ 1( Copyright ' 2(1$ )earson ducation* +nc, 2-) Choose the enantiomer of the compound &elo!, A) B) C) D) ) Ans!er" #ection" $%$ 2.) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" the same compound #ection" $%$ 11 Copyright ' 2(1$ )earson ducation* +nc, 20) 7he compound CH 3 CHClCH 2 CH8CHCH 2 CH 3 contains only one asymmetric center, 1plain !hy it has four stereoisomers, Ans!er" +n addition to the single asymmetric center !hich may &e either R or S* it also contains a car&on%car&on dou&le &ond !hich may &e either E or Z, 7hus* the four stereoisomers can &e designated E* R9 E* S9 Z* R9 and Z* S, #ection" $%- 22) Dra! the enantiomer of the compound &elo!, Ans!er" #ection" $%. 23) +dentify the follo!ing compounds as R or S, A) S, S, R B) S, R, S C) R, S, S D) S, S, S ) R, R, R Ans!er" D #ection" $%. 12 Copyright ' 2(1$ )earson ducation* +nc, 3() +dentify all pairs of enantiomers, A) B and D* A and C B) A and C C) B and D D) A and B* A and D* B and C* C and D ) B and D* A and B* A and D* B and C* C and D Ans!er" C #ection" $%. 31) +dentify all identical compounds, A) B and D* A and C B) A and C C) B and D D) A and B* A and D* B and C* C and D ) B and D* A and B* A and D* B and C* C and D Ans!er" B #ection" $%. 13 Copyright ' 2(1$ )earson ducation* +nc, 32) Which of the follo!ing compounds has an S configuration? A) B) C) D) ) Ans!er" B #ection" $%0 1$ Copyright ' 2(1$ )earson ducation* +nc, 33) Which of the follo!ing compounds has an R configuration? A) B) C) D) ) Ans!er" A #ection" $%0 3$) Which of the follo!ing groups has the highest priority using the Cahn* +ngold* )relog rules? A) B) C) :OH D) :O:CH 3 ) Ans!er" D #ection" $%0 1- Copyright ' 2(1$ )earson ducation* +nc, 3-) 7he configuration of R%6;)%glyceraldehyde is as follo!s" What is the a&solute configuration of 6%)%lactic acid? A) R configuration B) L configuration C) S configuration D) R and S configuration ) D and L configuration Ans!er" A #ection" $%0 3.) +ndicate !hether each of the follo!ing structures has the R or S configuration, What is the relationship &et!een the t!o structures? Ans!er" 7herefore* the t!o compounds are enantiomers, #ection" $%0 1. Copyright ' 2(1$ )earson ducation* +nc, 30) <a&el each asymmetric center in the compound &elo! as R or S, Ans!er" #ection" $%0 32) Dra! the structure of 6S)%1%&romo%1%chloropropane, 7a=e particular care to indicate three% dimensional stereochemistry detail properly, Ans!er" #ection" $%0 33) )ro/ide the structure of 6R)%$%octanol, Be careful to indicate proper stereochemistry, Ans!er" #ection" $%0 $() +dentify the follo!ing compounds as R or S, A) R, S, R B) S, R, R C) S, S, S D) R, R, R ) S, S, R Ans!er" A #ection" $%0 10 Copyright ' 2(1$ )earson ducation* +nc, $1) )ro/ide a careful structure for 62R,3S)%2*3%di&romohe1ane, Ans!er" #ection" $%0 $2) )ro/ide a careful structure for 62S,3S)%2*3%di&romohe1ane, Ans!er" #ection" $%0 $3) )ro/ide a careful structure for 62S,3R)%2*3%di&romohe1ane, Ans!er" #ection" $%0 $$) <a&el each asymmetric center as > or #, Ans!er" #ection" $%0 12 Copyright ' 2(1$ )earson ducation* +nc, $-) )ro/ide a careful structure for 62>*3#*$#)%2%&romo%$%methyl%3%he1anol, Ans!er" #ection" $%0 $.) )ro/ide a careful structure for 62S,3R,4R)%2%&romo%$%methyl%3%he1anol, Ans!er" #ection" $%0 $0) Which of the follo!ing is a true statement? A) All chiral molecules possess a plane of symmetry, B) All achiral molecules are meso, C) All molecules !hich possess a single chirality center of the S configuration are le/orotatory, D) A mi1ture of achiral compounds !ill &e optically inacti/e, ) All molecules !hich possess t!o or more chirality centers !ill &e chiral, Ans!er" D #ection" $%2 $2) Which of the follo!ing is not true of enantiomers? A) 7hey ha/e the same melting point, B) 7hey ha/e the same &oiling point, C) 7hey ha/e the same chemical reacti/ity !ith non%chiral reagents, D) 7hey ha/e the same density, ) 7hey ha/e the same specific rotation, Ans!er" #ection" $%3 13 Copyright ' 2(1$ )earson ducation* +nc, $3) Which of the follo!ing is?are optically inacti/e? A) a -(%-( mi1ture of R and S enantiomers B) a meso compound C) e/ery achiral compound D) a racemic mi1ture ) all the a&o/e Ans!er" #ection" $%3 -() Which of the follo!ing statements correctly pertains to a pair of enantiomers? A) 7hey rotate the plane of polari@ed light &y e1actly the same amount and in opposite directions, B) 7hey rotate the plane of polari@ed light &y differing amounts and in opposite directions, C) 7hey rotate the plane of polari@ed light &y differing amounts and in the same direction, D) 7hey ha/e different melting points, ) 7hey ha/e the same melting point* &ut they ha/e different &oiling points, Ans!er" A #ection" $%3 -1) +f 6S)%glyceraldehyde has a specific rotation of %2,0A* !hat is the specific rotation of 6R)% glyceraldehyde? A) %2,0A B) ;2,0A C) (,(A D) cannot &e determined from the information gi/en Ans!er" B #ection" $%3 -2) A mi1ture of eBual amounts of t!o enantiomers CCCCCCCC, A) is called a racemic mi1ture B) is optically inacti/e C) implies that the enantiomers are meso forms D) &oth A and B ) none of the a&o/e Ans!er" D #ection" $%3 -3) A solution containing (,3. g of 2%&romooctane in 1( m< ether solution ga/e an o&ser/ed rotation of %1,2A in a 1( cm cell at Calculate the specific rotation of this solution, Ans!er" DEF 8 DEF 8 8 %12,0-A in ether #ection" $%3 2( Copyright ' 2(1$ )earson ducation* +nc, -$) A ne!ly isolated natural product !as sho!n to &e optically acti/e, +f a solution of 2,( g in 1( m< of ethanol in a -( cm tu&e gi/es a rotation of ;2,-0A* !hat is the specific rotation of this natural product? Ans!er" ;2,-0A #ection" $%3 --) 7!enty grams of a compound !as dissol/ed in 1(( m< of sol/ent and ga/e an o&ser/ed rotation of %2( degrees, 7he sample tu&e is $ dm long, Calculate the specific rotation, Ans!er" %2-A #ection" $%3 -.) 7he specific rotation of a pure su&stance is 1,.2A, What is the specific rotation of a mi1ture containing 0-G of this isomer and 2-G of the 6%) isomer? A) ;1,.2A B) (A C) ;1,2.A D) ;(,2$A ) ;,($2A Ans!er" D #ection" $%1( -0) 7he specific rotation of a pure su&stance is %-,3(A, What is the percentage of this isomer in a mi1ture !ith an o&ser/ed specific rotation of %2,3-A? A) 2-G B) -(G C) 0-G D) 2(G ) (G Ans!er" C #ection" $%1( -2) 6%)%Handelic acid has a specific rotation of %1-2A, What !ould &e the specific rotation of a solution !hich contains $(G 6%)%mandelic acid and .(G 6;)%mandelic acid? A) ;3-A B) ;.3A C) ;32A D) %32A ) %.3A Ans!er" C #ection" $%1( -3) 7he specific rotation of 6R)%6;)%glyceraldehyde is ;2,0A, +f a mi1ture of glyceraldehydes enantiomers is 2(G S and 2(G R* !hat is the specific rotation of the mi1ture? Ans!er" %-,2A #ection" $%1( 21 Copyright ' 2(1$ )earson ducation* +nc, .() A sample of 6;) and 6%)%3%chlorohe1ane has a rotation of %2( degrees, )ure 6;) %3% chlorohe1ane has a rotation of ;$( degrees, Calculate the enantiomeric e1cess and the amount of 6%) and 6;)%3%chlorohe1ane in the original sample, Ans!er" -(G* 0-G 6%)* 2-G 6;) #ection" $%1( .1) What is the relationship &et!een the follo!ing compounds? A) superimposa&le !ithout &ond rotation B) constitutional isomers C) conformational isomers D) diastereomers ) enantiomers Ans!er" #ection" $%11 .2) What is the relationship &et!een the structures sho!n &elo!? A) enantiomers B) diastereomers C) configurational isomers D) identical compounds ) constitutional isomers Ans!er" B #ection" $%11 22 Copyright ' 2(1$ )earson ducation* +nc, .3) What is the relationship &et!een the follo!ing compounds? A) enantiomers B) diastereomers C) constitutional isomers D) conformational isomers ) identical compounds Ans!er" A #ection" $%11 .$) What is the relationship &et!een the follo!ing compounds? A) enantiomers B) diastereomers C) constitutional isomers D) conformational isomers ) identical compounds Ans!er" B #ection" $%11 .-) Which of the follo!ing is chiral? A) cis%1%&romo%3%chlorocyclo&utane B) trans%1%&romo%3%chlorocyclo&utane C) cis%1*$%dimethylcyclohe1ane D) cis%1*3%dimethylcyclohe1ane ) trans%1*3%dimethylcyclohe1ane Ans!er" #ection" $%11 23 Copyright ' 2(1$ )earson ducation* +nc, ..) Ho! many diastereomers e1ist for the compound &elo!? A) 2 B) $ C) . D) 0 ) 2 Ans!er" C #ection" $%11 .0) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" enantiomers #ection" $%11 .2) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" diastereomers #ection" $%11 2$ Copyright ' 2(1$ )earson ducation* +nc, .3) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" diastereomers #ection" $%11 0() Dra! the structure of 62R*3S)%dichloropentane, 7a=e particular care to indicate three% dimensional stereochemistry detail properly, Ans!er" #ection" $%11 01) Dra! the structure of 62S*3R)%dichloropentane, 7a=e particular care to indicate three% dimensional stereochemistry detail properly, Ans!er" #ection" $%11 02) Dra! the structure of any diastereomer of 62R*3S)%dichloropentane, 7a=e particular care to indicate three%dimensional stereochemistry detail properly, Ans!er" #ection" $%11 03) #teroisomers !hich are not mirror image isomers are CCCCCCCC, Ans!er" diastereomers #ection" $%11 2- Copyright ' 2(1$ )earson ducation* +nc, 0$) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" the same compound #ection" $%11 0-) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" the same compound #ection" $%11 0.) Which of the follo!ing terms &est descri&es the pair of compounds sho!n" enantiomers* diastereomers* or the same compound? Ans!er" enantiomers #ection" $%11 00) Dra! the stereoisomers of 1*3%dichlorocyclopentane, Ans!er" #ection" $%11 2. Copyright ' 2(1$ )earson ducation* +nc, 02) )ro/ide a perspecti/e dra!ing of 62R*3S)%1*2*3%trichloropentane, Ans!er" #ection" $%11 03) )ro/ide a perspecti/e dra!ing of the enantiomer of 62R*3S)%1*2*3%trichloropentane, Ans!er" #ection" $%11 2() )ro/ide a perspecti/e dra!ing of each diastereomer of 62R*3S)%1*2*3%trichloropentane, Ans!er" #ection" $%11 21) +dentify all pairs of diastereomers, A) B and D* A and C B) A and C C) B and D D) A and B* A and D* B and C* C and D ) B and D* A and B* A and D* B and C* C and D Ans!er" D #ection" $%11 20 Copyright ' 2(1$ )earson ducation* +nc, 22) +dentify all meso compounds, A) B and D* A and C B) A and C C) B and D D) A and B* A and D* B and C* C and D ) B and D* A and B* A and D* B and C* C and D Ans!er" B #ection" $%11 23) +dentify all configurational isomers, A) B and D* A and C B) A and C C) B and D D) A and B* A and D* B and C* C and D ) B and D* A and B* A and D* B and C* C and D Ans!er" #ection" $%11 22 Copyright ' 2(1$ )earson ducation* +nc, 2$) Which of the follo!ing is a meso compound? A) B) C) D) ) Ans!er" A #ection" $%13 23 Copyright ' 2(1$ )earson ducation* +nc, 2-) What is the relationship &et!een the follo!ing compounds? A) enantiomers B) diastereomers C) constitutional isomers D) conformational isomers ) identical compounds Ans!er" #ection" $%13 2.) Which of the follo!ing is a meso compound? A) trans%1* $%dimethylcyclohe1ane B) cis%1* 3%dimethylcyclohe1ane C) trans%1* 3%dimethylcyclohe1ane D) cis%1* $%dimethylcyclohe1ane ) trans%1* 2%dimethylcyclohe1ane Ans!er" B #ection" $%13 20) Ho! many stereoisomers e1ist !ith the follo!ing &asic connecti/ity? BrCH 2 CH6CH 3 )CH 2 CH 3 A) ( B) 1 C) 2 D) $ ) 2 Ans!er" C #ection" $%13 22) Ho! many stereoisomers e1ist !ith the follo!ing &asic connecti/ity? CH 3 CHClCH 2 CHClCH 3 A) ( B) 1 C) 2 D) 3 ) $ Ans!er" D #ection" $%13 3( Copyright ' 2(1$ )earson ducation* +nc, 23) Which of the statements &elo! correctly descri&es an achiral molecule? A) 7he molecule has a nonsuperimposa&le mirror image, B) 7he molecule e1hi&its optical acti/ity !hen it interacts !ith plane%polari@ed light, C) 7he molecule has an enantiomer, D) 7he molecule might &e a meso form, ) none of the a&o/e Ans!er" D #ection" $%13 3() Consider the molecules !ith molecular formula C 2 H 2 Br 2 Cl 2 , a) Dra! a structure that is optically inacti/e &ecause it does not ha/e an asymmetric center, &) Dra! a structure that is optically inacti/e &ecause it is a meso compound, c) Dra! a structure that is optically acti/e &ecause it is chiral, Ans!er" a) no chirality center &) meso compound c) chiral #ection" $%13 31 Copyright ' 2(1$ )earson ducation* +nc, 31) Dra! the structure of a meso form of 1*3%dichlorocyclopentane, 7a=e particular care to indicate three%dimensional stereochemistry detail properly, Ans!er" #ection" $%13 32) <a&el the molecule sho!n as chiral or achiral, Ans!er" Achiral #ection" $%13 33) <a&el the molecule sho!n as chiral or achiral, Ans!er" Chiral #ection" $%13 3$) <a&el the molecule sho!n as chiral or achiral, Ans!er" Achiral #ection" $%13 32 Copyright ' 2(1$ )earson ducation* +nc, 3-) <a&el the molecule sho!n as chiral or achiral, Ans!er" Chiral #ection" $%13 3.) +s the molecule sho!n chiral? +s it a meso compound? Ans!er" not chiral9 not meso #ection" $%13 30) +s the molecule sho!n chiral? +s it a meso compound? Ans!er" not chiral9 not meso #ection" $%13 32) +s the molecule sho!n chiral? +s it a meso compound? Ans!er" not chiral* meso #ection" $%13 33 Copyright ' 2(1$ )earson ducation* +nc, 33) +s the molecule sho!n chiral? +s it a meso compound? Ans!er" not chiral9 not meso #ection" $%13 1(() What is the configuration of the follo!ing compound? A) 2S* 3R B) 3R* 3S C) 2S* 3S D) 2R* 3R ) CanIt do R and S9 the compound is achiral, Ans!er" C #ection" $%1$ 3$ Copyright ' 2(1$ )earson ducation* +nc, 1(1) +n the Jischer proKection &elo!* !hat are the configurations of the t!o asymmetric centers? A) 2R* 3R B) 2R* 3S C) 2S* 3R D) 2S* 3S ) cannot &e determined from structure Ans!er" A #ection" $%1$ 1(2) <a&el each asymmetrical car&on in the compound &elo! as R or S, Ans!er" #ection" $%1$ 3- Copyright ' 2(1$ )earson ducation* +nc, 1(3) Dra! a perspecti/e formula of 62R*3S)%3%&romo%2%&utanol, Ans!er" #ection" $%1$ 1($) Dra! any diastereomer of 62R*3R)%2*3%dichloropentane, Be careful to indicate proper stereochemistry, Ans!er" #ection" $%1$ 1(-) Can one predict !hether a compound !ith a single asymmetric center is de1tro% or le/orotatory &ased on the R/S assignment at this asymmetric center? 1plain &riefly, Ans!er" Lo, R/S assignment is purely a con/ention of nomenclature and is completely independent of the direction in !hich plane%polari@ed light is rotated &y the compound, #ection" $%1$ 1(.) Assign an R or S configurational la&el to each asymmetric center in the molecule &elo!, Ans!er" #ection" $%1$ 3. Copyright ' 2(1$ )earson ducation* +nc, 1(0) 5i/e the complete name6s) of the follo!ing compound, Ans!er" 62R, 4S)%2*$%dichloropentane or 62S, 4R)%2*$%dichloropentane #ection" $%1$ 1(2) Briefly descri&e ho! t!o enantiomers might &e separated, Ans!er" 7he t!o compounds can &e con/erted to diastereomers* separated &ased on different physical properties of these diastereomers* and su&seBuently returned to their original forms or chromatographic separation using a chiral stationary phase, #ection" $%1- 1(3) 7he compound &elo! contains an asymmetric center at nitrogen, Why canIt indi/idual stereoisomers of this compound &e isolated at room temperature? Ans!er" Litrogen has a pair of non&onding electrons that allo! it to turn Minside outM at room temperature, Because of rapid in/ersion* the indi/idual stereoisomers cannot &e isolated, #ection" $%1. 11() +dentify the compounds that ha/e an asymmetric center, A) A B) B C) C D) A and B ) A* B* and C Ans!er" #ection" $%1. 30 Copyright ' 2(1$ )earson ducation* +nc, 111) +dentify the pair of compounds, A) identical B) conformational isomers C) constitutional isomers D) configurational isomers ) none of the a&o/e Ans!er" C #ection" $%32 32 Copyright ' 2(1$ )earson ducation* +nc,