Carbon'Compounds'Spring'2013'Home%Work%2%%Due%date:%February%25,%by%the%end%of%the%class%10:20%am%(assignments%turned%later%than%that%will%not%be%accepted).%%%%%%%%%%%%%%%%%%%%%'1)%Give%common%names%to%the%following%aromatic%compounds:%'Benzene:''''''Toluene:''''''''Benzaldehyde:''''''''Phenol:'''''''''Benzoic'Acid:'''''''''Aniline:''''2)%Give%structures%for%the%following%IUPAC%names:%'m?Bromochlorobenzene''''''p?Chloroaniline'''''''p?Bromotoluene'''''''2,6?Dibromophenol'''''''m?Chlorobenzoic'acid''''''2,4,6?Trinitrotoluene'(TNT)''''''Nitrobenzene'''''3)%Why%benzene%ring%goes%through%the%reaction%of%substitution%and%not%through%the%reaction%of%addition?%(hint:%use%hybridization%concept%to%explain%this)%''Due'to'the'aromaticity'of'the'benzene'ring.''''4)%Write%down%the%products%of%the%following%reactions,%name%each%reaction%and%show%the%mechanism%of%each%reaction.%''''''' ''''''''''''''' ''''''''''''''''''+HNO3[ H+ ]NO2+H3O+FeBr3Br2Br+HBr+AlCl3Cl+AlCl3ClO5)%In%the%secondary%susbstitution,%some%groups%are%meta%directors%and%some%are%ortho/para%directors.%Show%the%products%of%the%following%chemical%reactions.%For%one%of%them%(your%choice)%show%detailed%mechanism%and%explain%the%nature%of%the%orientation%to%meta%(or%ortho/para)%position.%'''''''''''''''' '''''''''''''''+FeBr3Br2OHOHHBr+BrOHBr+FeBr3Br2COHCOHBr+ HBr+AlCl3ClONH2NH2+HClONH2O+AlCl3ClONO2NO2+HClO6)%Give%examples%of%some%chiral%molecule.%'''''7)%Show%stereogenic%centers%and%indicate%each%molecule%as%R%or%S%configuration.%Draw%their%enantiomers%(their%mirror%images).%''S,R'%%%R,S'''8)%Draw%the%structure%for%%'R?Ibuprofen''(You'can'look'up'the'structure'from'internet,'your'textbook'or'your'lecture'notes.'Locate'the'stereogenic'center'and'draw'it'in ' R'configuration)'''BrClF HOHOHNH2HCOOHNH2HHOOCNBrHCOOHNBrHHOOCCH3CO2HH(S)-Ibuprafen(active)H3CHO2CH(R)-Ibuprafen(inactive)9)%Assign%R%or%S%configuration%to%each%stereogenic%center%in%the%following%molecules:%''''10)%Give%examples%of%the%different%kind%of%isomers%in%the%following%summary%of%isomers:%'''''CH3HBrHOHH3CBrHH3CH3C OHHBrH3CHHOHH3CRRSSSRIsomers (same molecular formulaConstitutional IsomersStereoisomersDiastereomersEnantiomersCis-trans DiastereomersChiral Diastereomersbutane2-methylpropaneBrBrR-2-BromobutaneS-2-Bromobutane11)%Draw%the%structures%for%the%following%molecules:%'2?Chloro?3,3?dimethylhexane'''''2?Bromo?5?chloro?3?methylhexane''''''3,3?Dichloro?2?methyl'hexane'''''1?Chloro?1?methylcyclohexane''''Chlorocyclopentane'''''ClClBrCl ClClCl2?Bromobutane'(Draw'R'and'S'enantiomers)''''Chloromethane'''''''12)%Name%the%following%molecules:%%From%the%left%to%the%right:%'2?Bromo?3,3?dimethylbutane,''''''''''''''''''''''''''''''''Methylcyclohexane,''2?Bromo?2,3?dimethylbutane,''''''''''''''''''''''''''''''''Propylcyclohexane,''2?Bromo?3?chlorobutane,''''''''''''''''''''''''''''''''''''''''R?2?chlorobutane.''''BrRBrSBrBrBrClCl13)%Reactions%of%nucleophilic%substitution.%'Write%down%the%product%of%the%following%nucleophilic%substitution%reactions;%indicate%whether%the%reaction%goes%through%SN1%or%SN2%path,%and%show%the%mechanism%of%each%reaction.%'''This'reaction'proceeds'via'SN1'mechanism.'Bromoalkane'is'tertiary,'and'forms'tertiary'carbocation;'plus'nucleophile'is'weak.'1)'First'step:'dissociation'of'Br'ion'to'form'tertiary'carbocation:''''''''''2)'Second'step:'nucleophilic'attack'(observe'conservation'of'the'charge):'''''''%'3)'Proton'transfer:''''''''''Br+ CH3OHBrBrCH3OHOCH3HOCH3BrOCH3HHBr''This'reaction'proceeds'via'SN2'mechanism.'Bromoalkane'is'primary,'and'nucleophile'is'strong.''One'step'bimolecular'process:''''''''''This'reaction'proceeds'via'SN1'mechanism.'Bromoalkane'is'tertiary,'and'forms'tertiary'carbocation;'plus'nucleophile'is'weak'(mechanism'is'analogous'to'the'SN1'mechanism'above).'''%''''''''''''Br+ Na