Practice(Packet:(Organic(Chemistry( Regents Chemistry: Mrs. Mintz. Practice(Packet( Chapter(8:(Organic(Chemistry(

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1 Practice(Packet:(Organic(Chemistry( Regents Chemistry: Mrs. Mintz Practice(Packet( Chapter(8:(Organic(Chemistry( 1

2 Organic!Chemistry" Hydrocarbons,!" Table!P!&!Table!Q" "! " Chemistry 200 Video Lesson 8.1 Objective:7 "! 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 General%properties%of%organic%compounds7 Types&of& bonds& present. Melting& Point. Boiling& Point.. Conductivity... "! contain!covalent!bonds!commonly! contain!c,!h,!o,!n,!s" tend!to!have!low!melting!pts,! many!are!liquids!or!gases!at!room! temp." tend!to!have!low!boiling!pts" poor!conductors!of!heat!or!" electricity!when!dissolved.!! Organic!acids!are!the!exception." General%properties%of%organic%compounds7 Molecular& Polarity.. Solubility... Rate&of& Reaction. "! most!organic!compounds!are!" nonpolar!!except!for!alcohols!&!" organic!acids." most!have!low!solubility!in!h 2 O" most!organic!rxns!are!slow" What!is!a!homologous!series?" "! "! H!a!group!of!substances!that!share!a!common!property." 2

3 .. &. Examples.. & Alkanes. Alkenes. Alkynes. CH 4 " methane" (First!" member)" C 3 H 8 " Propane" C 8 H 18 " Octane" "! Ethene!C 2 H 4 " (1st!member)" Propene!C 3 H 6 " Ethyne!C 2 H 2 " (1 st!member)" Propyne!C 3 H 4 " Saturated!Hydrocarbon:" "! H!contains!only!single!CHC!bonds" Propane7 C 3 H 8 7 Saturated!vs.!Unsaturated" Unsaturated!Hydrocarbon:" HH>"Alkanes&only. H!contains!at!least!one!multiple!Carbon!bond!! Butyne7 " "(double!or!triple)" C 4 H 6 7 Alkenes&&&Alkynes. 3

4 Organic( Formulas/ Video Lesson 8.2 Objectives/ Draw structural formulas from molecular formulas. Molecular(Formula/ Shows the kind and number of atoms in a compound only (generic recipe) o C 6 H 14 o C 6 H 12 O 6 Structural(Formula/ Shows the kind, # of atoms and bonding patterns (structures and approximate shapes) Molecular(formula(:(C 7 H 16 / Condensed(Structural( Formula/ Combination of both structural and molecular formulas All atoms coming off carbon are stated after each C CH 3 CH 2 CHCHCH 2 CH 3 / When(drawing(hydrocarbons,( you(must(always(have(4( bonds((8ek(around(each( element(except(for(h)/ Examples/ Molecular(Formula/ Structural(Formula/ Condensed(Structural(Formula/ C 3 H 8 / CH 3 CH 2 CH 3 / 4

5 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 CH 3 - methyl Naming(Organic( Compounds/ 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 (CH 3 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: CH 3!((((((/ ((((((((((((CH 3 CH CH 2 CH 3 STEP%1%%%%%Longest(chain(is(butane.( ' STEP%2%%%%%Number(chain.(((((((((CH 3!(((((((/ (((CH 3 CH CH 2 CH 3 / ((((1(((((((((2%%%%%%%3%%%%%%%4' STEP%3%%(Locate(substituents(and(name.((((/ / /2+Methylbutane /CH 2 =(CH( (CH 2 (CH 3 ( (((((1(((((((((2((((((((3((((((((((4/ /CH 3 (CH=CH (CH 3 / ((((1(( ((((((2((((((3((((((((4/ CH 3 / (((((((((((((((((((((((( / /CH 3 (CH=C CH 3 (((((4(((((((((3((((((2((((1/ /1KButene/ /2KButene/ /2KMethylK2Kbutene/ /CH 3 (C C( (CH /2KButyne/ 5

6 Functional*Groups* &** Table*R4 Chemistry 200 Video Lesson 8.3 Objective:9 How$do$we$use$Table$R$to$recognize$structural$ and$molecular$formulas$for$organic$molecules$ containing$functional$groups?$9 Creating$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' Substituted$Hydrocarbons9 4* 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 CH 3 CH 2 CH 2 CH 2 Br4 2*Bromobutane4 CH 3 CH 2 CHBrCH

7 1*Butanol4 CH 3 CH 2 CH 2 CH 2 OH4 *********2*Butanol4 CH 3 CH 2 CH 2 OHCH 3 4 Methyl*ethyl*ether4 Dimethyl*ether4 Diethyl*ether4 Methanal4 Ethanal4 Propanal4 Propanone4 Butanone4 3*Pentanone4 7

8 Functional*Groups* &** Table*R4 Chemistry 200 Video Lesson 8.4 Objective:9 How$do$we$use$Table$R$to$recognize$structural$ and$molecular$formulas$for$organic$molecules$ containing$functional$groups?$9 Methanoic*Acid4 Ethanoic*Acid4 Propanoic*Acid4 **have*strong*fragrant*aromas:*pineapples,*bananas,*wintergreen**4 Ammonia*!*NH 3 4 Methanamine4 Ethanamine4 8

9 Methanamide4 Ethanamide4 9

10 Isomers' Objectives' Identify structural isomers. Video Lesson 8.3 Isomers' Isomers are compounds that have the same simple molecular formula, but different structures. pentane' 23methyl3butane' 2,2393dimethyl3propane' Not3Isomers' 10

11 C 3 H 7 O' C 3 H 7 O' 11

12 Organic( Reactions. Objectives. Describe and classify different types of organic reactions. Video Lesson 8.5 7(Types(of(Organic( Reactions. 1. Combustion 2. Substitution 3. Addition 4. Esterification 5. Saponification 6. Fermentation 7. Polymerization Combustion. An alkane is burned in the presence of oxygen to produce water and carbon dioxide (O 2 is always a reactant!) Substitution. 1 or more hydrogen atom in a SATURATED ALKANE is replaced by another atom/group Addition. Atoms or groups are added at the multiple bond of an unsaturated hydrocarbon to become a saturated halocarbon (halide R;H(((+(((X 2 (((!((R;X(((+((HX. Alkane. Halogen. Halocarbon. Hydrogen(halide. 12

13 Esterification. Making soap Saponification. Fermentation. The production of alcohol (ethanol) Polymerization. Formation of large molecules called polymers C 2 H 4 + C 2 H 4! (C 2 H 4 ) 2 13

14 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 (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? (By(how(many(carbon(atoms(does(each(member(of(a(homologous(series(differ from(the(previous(member? (Which(of(the(following(is(a(saturated(hydrocarbon? 1. ethane 3. propene 2. ethyne 4. propane 14

15 Practice(Organic(Chemistry( 10. Which(compound(is(a(member(of(the(same(homologous(series(as(C3H6? 1. C2H4 3. C3H4 2. C2H6 4. C3H8 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 2. C2H4 3. C6H6 4. C6H (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? 15

16 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? 16

17 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!!!1,butyne! 17

18 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 f. 1Wheptyne 18

19 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 and(forms(the(basis(for(the(name(of(the(hydrocarbon. 2. 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. 3. Number(the(carbons(of(the(parent(chain(from(the(end(that(gives(the(substituents(the lowest(numbers. 4. 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.). 5. 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.( 19

20 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 20

21 Practice(Organic(Chemistry( Naming,Hydrocarbons, 1.( 5.( 2.( 6.( 3.( 7.( 4.( 8.( 21

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24 Practice(Organic(Chemistry( Video&Lesson&8.3:& Classify'each'of'the'following'structural'formulas'and'write'each'name' (( ( ( ( ((((( (( ( ( ((( ( ((((((( ( ( ( ( 24

25 Practice(Organic(Chemistry( ( ( ( ( (( ( Classify'each'name'and'draw'the'structural'formula' 2Rhexanol( ( ethyl(methyl(ether( 3(heptanol( 2(hexanone( butanal( 2(pentanone( 25

26 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' (( ( ( ( ( ( 26

27 Practice(Organic(Chemistry( ( ( ( ( (( ( Classify'each'name'and'draw'the'structural'formula' pentanoic(acid( methyl(ethanoate( 2Rpropanamine( ethyl(methanoate( methanoic(acid( ethanoic(acid( 27

28 Practice(Organic(Chemistry( propyl(ethanoate( methanamide( ethanamide( 1Rbutanamine( Video&Lesson&8.5:(Isomers( 28

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31 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.( 31

32 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( ( 32

33 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.( 33

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