Regents Chemistry: Mrs. Mintz...

Practice(Packet:(Organic(Chemistry(

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Regents Chemistry: Mrs. Mintz

Practice(Packet(Chapter(8:(Organic(Chemistry(

1

!"

Organic!Chemistry"Hydrocarbons,!"

Table!P!&!Table!Q"

"Chemistry 200

Video Lesson 8.1

!" What%is%a%hydrocarbon%and%the%properties%of%organic%molecules?%77How%do%we%use%table%P%and%Q%to%write%structural%and%molecular%formulas%for%hydrocarbons?7

Objective:7

!"

Types&of&bonds&present.Melting&Point.

Boiling&Point..

Conductivity...

General%properties%of%organic%compounds7

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."

!"Molecular&Polarity.

.Solubility.

..

Rate&of&Reaction.

General%properties%of%organic%compounds7

most!organic!compounds!are!"

nonpolar!!except!for!alcohols!&!"

organic!acids."

most!have!low!solubility!in!H2O"

most!organic!rxns!are!slow"

!" !"

What!is!a!homologous!series?"

H!a!group!of!substances!that!share!a!common!property."

2

!"

Alkanes. Alkenes. Alkynes...&.Examples..&........

CH4"

methane"

(First!"

member)"

C3H8"

Propane"

C8H18"

Octane"

Ethene!C2H4"

(1st!member)"

Propene!C3H6"

Ethyne!C2H2"

(1st!member)"

Propyne!C3H4"

!"

Saturated!Hydrocarbon:"

H!contains!only!single!CHC!bonds"

HH>"Alkanes&only.

Unsaturated!Hydrocarbon:"

H!contains!at!least!one!multiple!Carbon!bond!!

" "(double!or!triple)"

Saturated!vs.!Unsaturated"

Propane7C3H87

Alkenes&&&Alkynes.

Butyne7C4H67

3

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)oC6H14

oC6H12O6

Structural(Formula/• Shows the kind, # of atoms and bonding

patterns (structures and approximateshapes)

Molecular(formula(:(C7H16/

Condensed(Structural(Formula/

• Combination of both structural andmolecular formulas

• All atoms coming off carbon are stated aftereach C

CH3CH2CHCHCH2CH3/

When(drawing(hydrocarbons,(you(MUST(always(have(4(bonds((8eK(around(each(element(except(for(H)/

Examples/C3H8/Molecular(Formula/

Structural(Formula/

Condensed(Structural(Formula/ CH3CH2CH3/

4

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

Naming(Organic(Compounds/

1. Find the longest chain2. 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 Dio Trio 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─(CH3/ /2KButene/

((((1(( ((((((2((((((3((((((((4/CH3/

((((((((((((((((((((((((|//CH3─(CH=C─CH3 /2KMethylK2Kbutene/(((((4(((((((((3((((((2((((1/

/CH3─(C≡C(─(CH3 /2KButyne/

1 2 3 4

5

Functional*Groups*&**

Table*R4Chemistry 200

Video Lesson 8.3

How$do$we$use$Table$R$to$recognize$structural$and$molecular$formulas$for$organic$molecules$containing$functional$groups?$9

Objective:9

Creating$Structural$Formulas$from$a$Name9Steps:91.*Identify*&*draw*the*parent*chain.**The*parent*chain*is*the4longest*continuous*carbon*chain.**If*there*is*a*multiple*bond44in*the*molecule,*it*will*be*in*the*parent*chain*as*well4

2.*Add*any*wriBen*substitutes3.*Fill*molecule*w/*hydrogens*using*HONC*rule

Element' #)of)Bonds'H'O'N'C'

14243444

*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

1*Bromobutane4CH3CH2CH2CH2Br4

2*Bromobutane4CH3CH2CHBrCH34

6

1*Butanol4CH3CH2CH2CH2OH4

*********2*Butanol4CH3CH2CH2OHCH34

Dimethyl*ether4 Diethyl*ether4Methyl*ethyl*ether4

Propanal4Methanal4 Ethanal4 Propanone4 Butanone4 3*Pentanone4

7

Functional*Groups*&**

Table*R4Chemistry 200

Video Lesson 8.4

How$do$we$use$Table$R$to$recognize$structural$and$molecular$formulas$for$organic$molecules$containing$functional$groups?$9

Objective:9

Ethanoic*Acid4Methanoic*Acid4 Propanoic*Acid4

**have*strong*fragrant*aromas:*pineapples,*bananas,*wintergreen**4 Ammonia*!*NH34

Methanamine4 Ethanamine4

8

Methanamide4 Ethanamide4

9

Isomers'

Video Lesson 8.3

Objectives'• Identify structural isomers.

Isomers'• Isomers are compounds that have the same

simple molecular formula, but differentstructures.

pentane' 23methyl3butane' 2,2393dimethyl3propane'

Not3Isomers'

10

C3H7O' C3H7O'

11

Organic(Reactions.

Video Lesson 8.5

Objectives.• Describe and classify different types of

organic reactions.

7(Types(of(Organic(Reactions.

1. Combustion2.  Substitution3. Addition4. Esterification5.  Saponification6.  Fermentation7. Polymerization

Combustion.• An alkane is burned in the presence of

oxygen to produce water and carbondioxide (O2 is always a reactant!)

Substitution.• 1 or more hydrogen atom in a SATURATED

ALKANE is replaced by another atom/group

R;H(((+(((X2(((!((R;X(((+((HX.Alkane. Halogen. Halocarbon. Hydrogen(halide.

Addition.• Atoms or groups are added at the multiple bond of

an unsaturated hydrocarbon to become a saturated halocarbon (halide

12

Esterification.Saponification.

• Making soap

Fermentation.• The production of alcohol (ethanol)

Polymerization.• Formation of large molecules called

polymers• C2H4 + C2H4 ! (C2H4)2

13

Practice(Organic(Chemistry(


Video&Lesson&8.1:&&

Answer'the'following'questions.'

1. ____(All(organic(compounds(must(contain:1. hydrogen2. nitrogen

3. carbon4. oxygen

2. ____(Which(element(is(composed(of(atoms(that(can(form(more(than(one(covalentbond(with(one(another?

1. hydrogen2. helium

3. carbon4. calcium

3. ____(What(is(the(total(number(of(valence(electrons(in(a(carbon(atom(in(the(groundstate

1. 122. 2

3. 64. 4

4. ____(Which(property(is(generally(characteristic(of(an(organic(compound?1. low(melting(point2. high(melting(point

3. mainly(polar4. mainly(nonpolar

5. ____(In(general,(which(property(do(organic(compounds(share?1. high(melting(points2. high(electrical(conductivity3. readily(soluble(in(water4. slow(reaction(rate

6. ____(A(hydrocarbon(molecule(containing(one(triple(bond(is(classified(as(an:1. alkene2. alkane

3. alkyne4. alkadience

7. ____(What(is(the(total(number(of(hydrogen(atoms(in(a(molecule(of(butane?1. 102. 6

3. 84. 4

8. ____(By(how(many(carbon(atoms(does(each(member(of(a(homologous(series(differfrom(the(previous(member?

1. 12. 2

3. 34. 4

9. ____(Which(of(the(following(is(a(saturated(hydrocarbon?1. ethane2. ethyne

3. propene4. propane

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10. ____Which(compound(is(a(member(of(the(same(homologous(series(as(C3H6?1. C2H42. C2H6

3. C3H44. C3H8

11. ____(Which(hydrocarbon(is(a(member(of(the(series(with(the(general(formul(CnH2nR2?1. ethyne2. ethane

3. butane4. benzene

12. ____(Which(compound(belongs(to(the(alkene(series?1. C2H22. C2H4

3. C6H64. C6H14

13. ____(Which(type(of(bond(occurs(in(a(saturated(hydrocarbon(molecule?1. single(covalent2. double(covalent

3. triple(covalent4. ionic

14. ____(In(which(group(could(the(hydrocarbons(all(belong(to(the(same(homologousseries?

1. C2H2,(C2H4,(C2H62. C2H4,(C3H4,(C4H83. C2H4,(C2H6,(C3H64. C2H4,(C3H6,(C4H8

15. ____(Which(formula(represents(butane?1. CH3CH32. CH3CH2CH33. CH3CH2CH2CH34. CH3CH2CH2CH2CH3

16. ____(Which(formula(represents(an(unsaturated(hydrocarbon?

(

15



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,

1. Based(upon(Figure(2(and(your(knowledge(of(alkenes,(why(does(the(compoundmethene(not(exist?

2. Why(do(the(carbon(atoms(with(the(double(bond(contain(1(less(Hydrogen(atoms(thencarbon(atoms(that(contains(a(single(bond?

ethene' ''propene' butene'

16



3. Using(Tables(P(and(Q,(draw(the(structural(formula(for(the(following(alkenes.((Nameeach(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



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(followingalkynes.(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



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(chainand(forms(the(basis(for(the(name(of(the(hydrocarbon.

2. Identify(all(of(the(substituents((groups(branching(from(the(parent(chain).(Thesubstituents(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(thelowest(numbers.

4. If(the(same(substituent(occurs(more(than(once,(the(location(of(each(point(on(whichthe(substituent(occurs(is(given.(In(addition,(the(number(of(times(the(substituentgroup(occurs(is(indicated(by(a(prefix((di,(tri,(tetra,(etc.).

5. If(there(are(two(or(more(different(substituents(they(are(listed(in(alphabetical(orderusing(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



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



Naming,Hydrocarbons,

1.( 5.(

2.( 6.(

3.( 7.(

4.( 8.(

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Video&Lesson&8.3:&

Classify'each'of'the'following'structural'formulas'and'write'each'name'

________________________________(( _________________________( ________________________(

______________________________( (((((_____________________(( ___________________________(

_________________________( (((_______________________________( (((((((____________________________(

_______________________________( ___________________________( ________________________(

24



_______________________________( _____________________________( ________________________(

__________________________( ________________________________(( ________________________________(

Classify'each'name'and'draw'the'structural'formula'

2Rhexanol( ( ethyl(methyl(ether(

3(heptanol( 2(hexanone(

butanal( 2(pentanone(

25



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



____________________________( ___________________________( ________________________(

_______________________________( ________________________(( _____________________________(

Classify'each'name'and'draw'the'structural'formula'

pentanoic(acid( methyl(ethanoate(

2Rpropanamine( ethyl(methanoate(

methanoic(acid( ethanoic(acid(

27



propyl(ethanoate( methanamide(

ethanamide( 1Rbutanamine(

Video&Lesson&8.5:(Isomers(

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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



dehydration'

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.(

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



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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Regents Chemistry: Mrs. Mintz...

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