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Practice(Packet:(Organic(Chemistry( Regents Chemistry: Mrs. Mintz Practice(Packet( Chapter(8:(Organic(Chemistry( http://mintzchemistry.weebly.com( 1 Objective:7 Organic!Chemistry" "! What%is%a%hydrocarbon%and%the%properties%of% organic%molecules?%7 7 How%do%we%use%table%P%and%Q%to%write% structural%and%molecular%formulas%for% hydrocarbons?7 Hydrocarbons,!" Table!P!&!Table!Q" "! Chemistry 200 Video Lesson 8.1 General%properties%of%organic%compounds7 General%properties%of%organic%compounds7 "! "! Types&of& bonds& present. contain!covalent!bonds!commonly! contain!C,!H,!O,!N,!S" Molecular& most!organic!compounds!are!" Polarity. nonpolar!!except!for!alcohols!&!" Melting& Point. tend!to!have!low!melting!pts,! many!are!liquids!or!gases!at!room! temp." . Solubility. most!have!low!solubility!in!H2O" Boiling& Point. tend!to!have!low!boiling!pts" organic!acids." . . Rate&of& Reaction. . poor!conductors!of!heat!or!" Conductivity. electricity!when!dissolved.!! . Organic!acids!are!the!exception." most!organic!rxns!are!slow" . What!is!a!homologous!series?" H!a!group!of!substances!that!share!a!common!property." "! "! 2 Alkanes. . . . &. Examples. Alkenes. "! CH4" methane" Ethene!C2H4" (First!" (1st!member)" member)" Saturated!vs.!Unsaturated" Alkynes. "! Saturated!Hydrocarbon:" Ethyne!C2H2" (1st!member)" H!contains!only!single!CHC!bonds" &. Propane7 C3H87 . . . C3H8" . Propane" . Propene!C3H6" Propyne!C3H4" Unsaturated!Hydrocarbon:" H!contains!at!least!one!multiple!Carbon!bond!! " "(double!or!triple)" Butyne7 C4H67 Alkenes&&&Alkynes. . . HH>"Alkanes&only. C8H18" Octane" 3 Objectives/ • Draw structural formulas from molecular formulas. Organic( Formulas/ Video Lesson 8.2 Molecular(Formula/ Structural(Formula/ • Shows the kind and number of atoms in a compound only (generic recipe) o C6H14 o C6H12O6 • Shows the kind, # of atoms and bonding patterns (structures and approximate shapes) Molecular(formula(:(C7H16/ Condensed(Structural( Formula/ Examples/ Molecular(Formula/ • Combination of both structural and molecular formulas • All atoms coming off carbon are stated after each C When(drawing(hydrocarbons,( CH3CH2CHCHCH2CH3/ C3H8/ Structural(Formula/ you(MUST(always(have(4( bonds((8eK(around(each( element(except(for(H)/ Condensed(Structural(Formula/ 4 CH3CH2CH3/ Naming(Organic( Compounds/ Alkyl(Group/ • Also hydrocarbons, but have 1 less hydrogen than the corresponding alkane. • Use the same prefix found on Table P that corresponds to the number of carbons. • Alkly’s will end in –yl • CH3 - methyl 1. Find the longest chain 2. Number the hydrocarbon with the lowest number on the double or triple bond (if necessary) 3. Name the alkyl (CH3 – methyl) group (if it has one) 4. # the chain with the lowest number on the alkyl group or substituent in alkanes only. 5. Use prefix if more than 1 alkyl group o Di o Tri o tetra Give(the(name(of: CH3 !((((((/ ((((((((((((CH3─CH─CH2─CH3 STEP%1%%%%%Longest(chain(is(butane.( ' STEP%2%%%%%Number(chain.(((((((((CH3 !(((((((/ (((CH3─CH─CH2─CH3/ ((((1(((((((((2%%%%%%%3%%%%%%%4' STEP%3%%(Locate(substituents(and(name.((((/ / /2+Methylbutane /CH2=(CH(─(CH2─(CH3( /1KButene/ (((((1(((((((((2((((((((3((((((((((4/ /CH3─(CH=CH─(CH/3 ((((1(( ((((((2((((((3((((((((4/ CH3/ ((((((((((((((((((((((((|/ /CH3─(CH=C─CH3 (((((4(((((((((3((((((2((((1/ /CH3─(C≡C(─(CH3 1 5 2 3 4 /2KButene/ /2KMethylK2Kbutene/ /2KButyne/ Objective:9 Functional*Groups* How$do$we$use$Table$R$to$recognize$structural$ and$molecular$formulas$for$organic$molecules$ containing$functional$groups?$9 &** Table*R4 Chemistry 200 Video Lesson 8.3 Creating$Structural$Formulas$from$a$Name9 Steps:9 1.*Identify*&*draw*the*parent*chain.**The*parent*chain*is*the 4longest*continuous*carbon*chain.**If*there*is*a*multiple*bond4 4in*the*molecule,*it*will*be*in*the*parent*chain*as*well4 2.*Add*any*wriBen*substitutes 3.*Fill*molecule*w/*hydrogens*using*HONC*rule Element' H' O' N' C' #)of)Bonds' 14 24 34 44 4* Substituted$Hydrocarbons9 A*substituted*hydrocarbon*contains*side*groups*that*have* been*added*by*removing*hydrogens.**These*side*groups* could*be*hydrocarbons*or*they*could*be*other*elements.** Thus*some*substituted*hydrocarbons*are*not*even* hydrocarbons.**The*following*list*contains*substituted* groups*that*you*should*know.4 1*Bromobutane4 CH3CH2CH2CH2Br4 1 6 2*Bromobutane4 CH3CH2CHBrCH34 1*Butanol4 CH3CH2CH2CH2OH4 Methanal4 *********2*Butanol4 CH3CH2CH2OHCH34 Ethanal4 Methyl*ethyl*ether4 Dimethyl*ether4 Propanone4 Propanal4 7 Butanone4 Diethyl*ether4 3*Pentanone4 Objective:9 Functional*Groups* How$do$we$use$Table$R$to$recognize$structural$ and$molecular$formulas$for$organic$molecules$ containing$functional$groups?$9 &** Table*R4 Chemistry 200 Video Lesson 8.4 Ethanoic*Acid4 Propanoic*Acid4 Methanoic*Acid4 Ammonia*!*NH34 **have*strong*fragrant*aromas:*pineapples,*bananas,*wintergreen**4 Methanamine4 8 Ethanamine4 Methanamide4 Ethanamide4 9 Objectives' • Identify structural isomers. Isomers' Video Lesson 8.3 Isomers' • Isomers are compounds that have the same simple molecular formula, but different structures. pentane' Not3Isomers' 10 23methyl3butane' 2,2393dimethyl3propane' C3H7O' C3H7O' 11 Objectives. Organic( Reactions. • Describe and classify different types of organic reactions. Video Lesson 8.5 7(Types(of(Organic( Reactions. Combustion. 1. Combustion 2. Substitution 3. Addition 4. Esterification 5. Saponification 6. Fermentation 7. Polymerization • An alkane is burned in the presence of oxygen to produce water and carbon dioxide (O2 is always a reactant!) Substitution. Addition. • 1 or more hydrogen atom in a SATURATED ALKANE is replaced by another atom/group • Atoms or groups are added at the multiple bond of an unsaturated hydrocarbon to become a saturated halocarbon (halide R;H(((+(((X2(((!((R;X(((+((HX. Alkane. Halogen. Halocarbon. Hydrogen(halide. 12 Esterification. Saponification. • Making soap Polymerization. Fermentation. • Formation of large molecules called polymers • C2H4 + C2H4 ! (C2H4)2 • The production of alcohol (ethanol) 13 Practice(Organic(Chemistry( Video&Lesson&8.1:&& Answer'the'following'questions.' 1. ____(All(organic(compounds(must(contain: 1. hydrogen 2. nitrogen 3. carbon 4. oxygen 2. ____(Which(element(is(composed(of(atoms(that(can(form(more(than(one(covalent bond(with(one(another? 1. hydrogen 3. carbon 2. helium 4. calcium 3. ____(What(is(the(total(number(of(valence(electrons(in(a(carbon(atom(in(the(ground state 1. 12 3. 6 2. 2 4. 4 4. ____(Which(property(is(generally(characteristic(of(an(organic(compound? 1. low(melting(point 3. mainly(polar 2. high(melting(point 4. mainly(nonpolar 5. ____(In(general,(which(property(do(organic(compounds(share? 1. high(melting(points 2. high(electrical(conductivity 3. readily(soluble(in(water 4. slow(reaction(rate 6. ____(A(hydrocarbon(molecule(containing(one(triple(bond(is(classified(as(an: 1. alkene 3. alkyne 2. alkane 4. alkadience 7. ____(What(is(the(total(number(of(hydrogen(atoms(in(a(molecule(of(butane? 1. 10 3. 8 2. 6 4. 4 8. ____(By(how(many(carbon(atoms(does(each(member(of(a(homologous(series(differ from(the(previous(member? 1. 1 3. 3 2. 2 4. 4 9. ____(Which(of(the(following(is(a(saturated(hydrocarbon? 1. ethane 3. propene 2. ethyne 4. propane http://mintzchemistry.weebly.com( 14 Practice(Organic(Chemistry( 10. ____Which(compound(is(a(member(of(the(same(homologous(series(as(C3H6? 1. C2H4 3. C3H4 2. C2H6 C3H8 4. 11. ____(Which(hydrocarbon(is(a(member(of(the(series(with(the(general(formul(CnH2nR2? 1. ethyne 3. butane 2. ethane 4. benzene 12. ____(Which(compound(belongs(to(the(alkene(series? 1. C2H2 3. C6H6 2. C2H4 C6H14 4. 13. ____(Which(type(of(bond(occurs(in(a(saturated(hydrocarbon(molecule? 1. single(covalent 3. triple(covalent 2. double(covalent 4. ionic 14. ____(In(which(group(could(the(hydrocarbons(all(belong(to(the(same(homologous series? 1. C2H2,(C2H4,(C2H6 2. C2H4,(C3H4,(C4H8 3. C2H4,(C2H6,(C3H6 4. C2H4,(C3H6,(C4H8 15. ____(Which(formula(represents(butane? 1. CH3CH3 2. CH3CH2CH3 3. CH3CH2CH2CH3 4. CH3CH2CH2CH2CH3 16. ____(Which(formula(represents(an(unsaturated(hydrocarbon? ( http://mintzchemistry.weebly.com( 15 Practice(Organic(Chemistry( Video&Lesson&8.2:& Background:,Structural(formulas(show(the(arrangement(of(the(atoms(within(the( molecules(as(far(as(which(atoms(are(bonded(to(which(and(whether(single,(double(or( triple(bonds(are(used.( Figure'1:' Structural,formulas,for,alkanes:, !methane! !ethane! !propane! 1. Using(Tables(P(and(Q(in(your(reference(table,(draw(the(structural(formula(for(the following(alkanes.,,Name,each,compound. a. C4H10( b. C5H12 c. C6H14 Figure'2:''' Structural,Formulas,for,Alkenes, ethene' ''propene' butene' 1. Based(upon(Figure(2(and(your(knowledge(of(alkenes,(why(does(the(compound methene(not(exist? 2. Why(do(the(carbon(atoms(with(the(double(bond(contain(1(less(Hydrogen(atoms(then carbon(atoms(that(contains(a(single(bond? http://mintzchemistry.weebly.com( 16 Practice(Organic(Chemistry( 3. Using(Tables(P(and(Q,(draw(the(structural(formula(for(the(following(alkenes.((Name each(compound. a. C5H10( b. C6H12 c. C7H14 When(naming(alkenes(you(must(give(the(location(of(the(double(bond(in(the(name(when( there(are(more(than(3(carbon(atoms(in(the(compound.((You(do(this(by(numbering(the( carbon(atoms(and(stating(which(number(carbon(the(double(bond(is(on.(((You(can( number(the(carbon(atoms(from'left'to'right(or(right'to'left(which(ever(gives(the(double( bond(the(lowest(possible(numbered(location.((This(is(because(compounds(are(not( stationary(in(the(“real(world”(and(are(therefore(constantly(moving.(See(Figure(3(below.(( Figure'3:'' 1,butene! !!!!!!!!!!!!!!!2,butene!!!!!!!!! !!!1,butene! 1. Using(Figure(3(and(reference(tables(P(&(Q(name(the(following(compounds: Drawing(structural(formulas(for(alkynes(is(exactly(the(same(as(alkenes(except(they( contain(a(triple(bond(instead(of(a(double(bond.((( Figure'4:' Structural'Formulas'for'alkynes' !!!!!!!!!!!!!!!1,!!butyne! !!!!2,butyne! http://mintzchemistry.weebly.com( 17 !!1,butyne! Practice(Organic(Chemistry( 1. Why(do(the(carbons(with(the(triple(bond(contain(no(bonded(hydrogen(atoms? 2. Using(Reference(Tables(P(and(Q,(draw(the(structural(formula(for(the(following alkynes.(Name(each(compound. a. C5H8( b. C6H10 c. C7H12 3. Name(the(following(compounds: Practice:,Draw'the'structural'formula'for'the'following'compounds:' a. C8H16 b. C4H6 c. 2Whexene d. 2Wheptyne e. 3Whexene http://mintzchemistry.weebly.com( 18 f. 1Wheptyne Practice(Organic(Chemistry( Chemists(use(a(system(developed(by(the(IUPAC((International(Union(of(Pure(and( Applied(Chemistry)(system(for(naming(isomers.(Here(is(a(simple(list(of(rules(to(follow.( Some(examples(are(given(at(the(end(of(the(list.(( 1. Identify(the(longest(continuous(carbon(chain.(This(chain(is(called(the(parent(chain 2. 3. 4. 5. and(forms(the(basis(for(the(name(of(the(hydrocarbon. Identify(all(of(the(substituents((groups(branching(from(the(parent(chain).(The substituents(are(named(using(the(proper(prefix((methW,(ethW,(etc)(and(a(–yl(ending. Number(the(carbons(of(the(parent(chain(from(the(end(that(gives(the(substituents(the lowest(numbers. If(the(same(substituent(occurs(more(than(once,(the(location(of(each(point(on(which the(substituent(occurs(is(given.(In(addition,(the(number(of(times(the(substituent group(occurs(is(indicated(by(a(prefix((di,(tri,(tetra,(etc.). If(there(are(two(or(more(different(substituents(they(are(listed(in(alphabetical(order using(the(base(name((ignore(the(prefixes). The!following!examples!will!illustrate!this:! **When'numbering,'the'parent'chain' determines'the'lowest'number.( (Draw(the(structural(formula(for(3WethylW5WmethylW3Wheptene.( http://mintzchemistry.weebly.com( 19 Practice(Organic(Chemistry( Structure,of,Hydrocarbons, 1. ethane 5. ethyne 2. propene 6. 3,3Wdimethyl(pentane 3. 2Wbutene 7. 2,3(–dimethyl(pentane 4. methane 8. 2Wbutyne http://mintzchemistry.weebly.com( 20 Practice(Organic(Chemistry( Naming,Hydrocarbons, 1.( 5.( 2.( 6.( 3.( 7.( 4.( 8.( http://mintzchemistry.weebly.com( 21 22 23 Practice(Organic(Chemistry( Video&Lesson&8.3:& Classify'each'of'the'following'structural'formulas'and'write'each'name' ________________________________(( ______________________________( _________________________( _________________________( (((((_____________________(( (((_______________________________( _______________________________( ___________________________( (((((((____________________________( ___________________________( http://mintzchemistry.weebly.com( 24 ________________________( ________________________( Practice(Organic(Chemistry( _______________________________( __________________________( _____________________________( ________________________________(( ________________________( ________________________________( Classify'each'name'and'draw'the'structural'formula' 2Rhexanol( ( ethyl(methyl(ether( 3(heptanol( 2(hexanone( butanal( 2(pentanone( http://mintzchemistry.weebly.com( 25 Practice(Organic(Chemistry( ethanal( dimethyl(ether( 3Rchloro(pentane( 4Rbromo(2Rpentyne( 1Riodo(propene( difluroRmethane( Video&Lesson&8.4:& Classify'each'of'the'following'structural'formulas'and'write'each'name' ________________________(( ___________________________( _________________________________( ___________________________( http://mintzchemistry.weebly.com( 26 ________________________( ________________________( Practice(Organic(Chemistry( ____________________________( ___________________________( _______________________________( ________________________(( ________________________( _____________________________( Classify'each'name'and'draw'the'structural'formula' pentanoic(acid( methyl(ethanoate( 2Rpropanamine( ethyl(methanoate( methanoic(acid( ethanoic(acid( http://mintzchemistry.weebly.com( 27 Practice(Organic(Chemistry( propyl(ethanoate( methanamide( ethanamide( 1Rbutanamine( Video&Lesson&8.5:(Isomers( http://mintzchemistry.weebly.com( 28 29 30 Practice(Organic(Chemistry( Video&Lesson&8.6:&(Organic(Reactions( Combustion:(Many(organic(compounds(react(with(excess(oxygen(to(form(carbon(dioxide( and(water.(On(Table(I(of(your(reference,(the(first(6(reactions(are(combustion(reactions.( Write(a(balance(reaction(for(the(combustion(of:( 1. Ethane: 2. Pentane: Substitution:,Saturated(hydrocarbons((ALKANES)(may(replace(a(hydrogen(atom(in(the( molecule(with(another(element((usually(a(halogen).( Example:(((((((((((((((((((C2H6(((+((((Cl2(((→((((C2H5Cl((((+((((HCl( Draw(the(structural(formulas(for(the(above(reaction:( Name(the(product(C2H5Cl_____________________________________( Write(a(balanced(reaction(for(the(substitution(of(bromine(onto(propane.( Draw(the(structure(of(and(name(two(possible(halocarbon(isomers(formed(in(the(above( reaction.( Addition:(Unsaturated(hydrocarbons((ALKENES(or(ALKYNES)(can(add(an(atom(of(hydrogen( or(of(a(halogen(at(the(site(of(a(double(or(triple(bond.((When(hydrogen(is(added,(the(process( is(called(HYDROGENATION.((When(a(halogen(is(added,(the(process(is(called( HALOGENATION.( C2H4(((((+(((((Br2((→((((C2H4Br2(( Name(the(product__________________________( Now(write(structural(formulas(for(the(addition(of(Cl2(onto(2R(butene.((Name(the(product.(( Notice(that,(unlike(substitution,(only(one(product(is(possible!( When(hydrogen(is(added(to(propene,(what(is(the(name(of(the(new(hydrocarbon(that(forms?( Write(a(balanced(equation(to(illustrate(this(reaction.( http://mintzchemistry.weebly.com( 31 Practice(Organic(Chemistry( Polymerization:(Large(molecules(can(form(when(individual(units(of(molecules( (monomers)(are(chained(together(to(form(a(polymer.((If(the(individual(monomer(is(an( unsaturated(hydrocarbon,(addition'polymerization(my(occur(as(the(double((or(triple)( bond(is(“broken(open”(and(a(chain(is(formed:( Esterification:,Esters(are(compounds(which(have(pleasant(odors.((They(are(formed(by(the( reaction(between(organic(acids(and(alcohols., Ethanoic(acid(and(methanol(will(react(to(form(methyl(ethanoate.(The(structural(formulas( for(this(reaction(are(shown(below.( dehydration' Now(draw(the(structures,(determine(the(products(and(name(each(reactant(and(organic( product(in(the(following(esterification(reactions:( C2H5COOH(((((((((+(((((C2H5OH(((→( HCOOH((((((+((((C3H7OH(((→( C3H7COOH(((+(((CH3OH(→( http://mintzchemistry.weebly.com( 32 Practice(Organic(Chemistry( Fermentation:,In(the(fermentation(process,(enzymes(found(in(living(things,(such(as(yeast,( convert(carbohydrates((usually(sugars)(into(carbon(dioxide(and(alcohol.((, Glucose((C6H12O6)(is(fermented(in(the(presence(of(the(enzyme(zymase(in(yeast(to(form( ethanol(and(carbon(dioxide.((Write(a(balanced(equation(to(represent(this(reaction:( Saponification:&The(hydrolysis(of(fats(by(basis(is(saponification(or(soap;making.((This( process(was(made(“famous”(by(a(scene(from(the(movie(“Fight(Club”.((The(main(characters(in( the(film(steal(human(fat(from(a(liposuction(clinic(and(react(it(with(lye((NaOH)(to(form(soap.((( The(reaction(looks(like(this:( (C17H35COO)3C3H5(((((+(((3(NaOH(((→(((C3H5(OH)3(((+(((3(C17H35COONa( The(presence(of(the(Na(and(the(NaOH(makes(this(reaction(very(recognizable!( Occasionally,(KOH(is(used(instead(of(NaOH….( http://mintzchemistry.weebly.com( 33 34 35 36 37 38 39 40 41