Chemistry chapter 20 LEC

8/13/2019 Chemistry chapter 20 LEC

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Chapter 20Organic

Chemistry

2008, Prentice Hall

Chemistry: A Molecular Approach , 1 st Ed. Nivaldo Tro

Roy KennedyMassachusetts Bay Community College

Wellesley Hills, MA


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Tro, Chemistry: A Molecular Approach 2

Structure Determines Properties Organic compounds all contain carbon

CO, CO 2 , carbonates and carbides are inorganicother common elements are H, O, N, (P, S)

Carbon has versatile bonding patternschains, rings, multiple bondschain length nearly limitless

Carbon compounds generally covalentmolecular; gases, liquids, or low melting solids;varying solubilities; nonconductive in liquid

C - C bonds unreactive (very stable)


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Bond Energies and Reactivities

C-C 347 kJ H 3 C-CH 3 NONREACTIVEIN AIR

S-S 214 kJ HS-SH EXTREMELYREACTIVE

Si-Si 213 kJ H 3 Si-SiH 3SPONTANEOUS

BURNS IN AIR

N-N 159 kJ H 2 N-NH 2EXTREMELY

REACTIVE

O-O 138 kJ HO-OH REACTIVE


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Allotropes of Carbon - Diamond


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Allotropes of Carbon - Graphite


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Carbon Bonding mainly forms covalent bonds C is most stable when it has 4 single covalent bonds,

but does form double and triple bondsC=C and C C are more reactive than CC C with 4 single bonds is tetrahedral,2 singles and 1 double is trigonal planar2 doubles or 1 triple and 1 single is linear


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8

Uses of Hydrocarbons Number of

C atomsState Major Uses

1-4 gasheating andcooking fuel

5-7liquids,

(low boiling)

solvents,

gasoline6-18 liquids gasoline

12-24 liquids jet fuel; campstove fuel

18-50liquids,

(high boiling)

diesel fuel,lubricants,heating oil

50+ solids petroleum jelly, paraffin wax

1-4 gasheating andcooking fuel

5-7liquids,

(low boiling)

solvents,

gasoline6-18 liquids gasoline

12-24 liquids jet fuel; campstove fuel

18-50liquids,

(high boiling)

diesel fuel,lubricants,heating oil

50+ solids petroleum jelly,

paraffin wax


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Saturated Hydrocarbons

a saturated hydrocarbon has all C-C single bonds

it is saturated with hydrogens

saturated aliphatic hydrocarbons are calledalkanes

chain alkanes have the general formula C nH2n+2


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Unsaturated Hydrocarbons

unsaturated hydrocarbons have one of more C=Cdouble bonds or C C triple bonds unsaturated aliphatic hydrocarbons that contain C=C

are called alkenesthe general formula of a monounsaturated chain alkene isCnH2n remove 2 more H for each additional unsaturation

unsaturated aliphatic hydrocarbons that contain C Care called alkynes

the general formula of a monounsaturated chain alkyne isCnH2n-2 remove 4 more H for each additional unsaturation
http://wps.prenhall.com/wps/media/objects/477/489271/st1802.htmlhttp://wps.prenhall.com/wps/media/objects/477/489271/st1802.html


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Aromatic Hydrocarbons

contain benzene ring structure even though they are often drawn with C=C,

they do not behave like alkenes


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alkanes

CH3

CH

C

H

CH3

CH3

CC

CH3

CH3

CH3

CH

CH2 C

H2

CH2

CH2

CH

alkenes

CH3

C C CH3

CH2

CH2

CH

2

C

H2

CH2

CH 2CH

2

C C C

H2

C

H2

CH2

CH2

CH

2

C

H2

CH2

alkynes


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15

Formulas molecular formulas just tell you what

kinds of atoms are in the molecule, butthey dont tell you how they are attached

structural formulas show you theattachment pattern in the molecule

models not only show you the attachment pattern, but give you an idea about theshape of the molecule


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Condensed Structural Formulas

attached atoms listed in order central atom with attached atoms

follow normal bonding patterns use to determine position of multiple bonds

() used to indicate more than 1 identicalgroup attached to same previous central

atom unless () group listed first in which case

attached to next central atom


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Line-Angle Formulas

each angle, and beginning and end represent a Catom

H omitted on Cincluded on functional groups

multiple bonds indicateddouble line is double bond, triple line is triple bond


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Formulas


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FormulasCH4 C

H

H

H

H

C2H6 CH3CH3 C

H

C

H

H

H

H

H

C3H8 CH3CH 2CH 3 C

H

C

H

H

H

C

H

H

H

H

C4H10 CH3CH 2CH 2CH 3 C

H

C

H

H

H

C

H

H

C

H

H

H

H

C4H10 C(CH 3)2 C

H

C

H

H

H

C

C

H

H

H

H

H

H


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Isomerism Isomers = different molecules with the same

molecular formula Structural Isomers = different pattern of atom

attachmentConstitutional Isomers

Stereoisomers = same atom attachments, differentspatial orientation


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Structural Isomers of C 4H10

Butane, BP = 0C Isobutane, BP = -12C

C C C C

H

H

H H

H H

H H

H

HC

H

H

H

H H

H

C HC

CH H

H


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Rotation about a bond is not isomerism


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Possible Structural IsomersCarbon

Content

Molecular

Formula

Possible

Isomers

4 C 4 H 10 2

5 C5H

12 3

6 C 6 H 14 5

7 C 7 H 16 9

8 C 8 H 18 189 C 9 H 20 35

10 C 10 H 22 75


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Ex 20.1 Write the structural formula and carbon

skeleton formula for C 6H14 start byconnecting

the carbonsin a line

determine

the Cskeleton ofthe otherisomers

C C C C C CC C C C C

C

C C C C C

CC C C C

C

CC C C C

C C


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fill in the Hto give eachC 4 bonds

C C C C

C

CH

H

H

H H H

H

H

HHH

HH

H

C C C C

C

C

H

H

H H H

HH

HH

H

H

H

H

H

C C C C C CH

H

H

H

H

H

H

H

H

H H

H

HH

Ex 20.1 Write the structural formula and carbonskeleton formula for C 6H14

C C C C

C

H

H

H H

HH

HH

H

HH

C H

H

H

C C C C C C

C C C C C

C

C C C C C

C

C C C C

C

CC C C C

C C

C C C C

C

H

H

H H

H

CHH

H

HHH

H

H

H


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convert eachto a carbonskeletonformula each bendand the endsrepresent Catoms

C C C C

C

CH

H

H

H H H

H

H

HHH

HH

H

C C C C

C

C

H

H

H H H

HH

HH

H

H

H

H

H

C C C C C CH

H

H

H

H

H

H

H

H

H H

H

HH

Ex 20.1 Write the structural formula and carbonskeleton formula for C 6H14

C C C C

C

H

H

H H

HH

HH

H

HH

C H

H

H

C C C C

C

H

H

H H

H

CHH

H

HH

H

H

H

H


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Stereoisomers

stereoisomers are different molecules whoseatoms are connected in the same order, but have

a different spatial direction optical isomers are molecules that are

nonsuperimposable mirror images of each other

geometric isomers are stereoisomers that arenot optical isomers


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Nonsuperimposable Mirror Images

mirror image cannot be rotated so all its atoms alignwith the same atoms of the original molecule


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Chirality

any molecule with a nonsuperimposable mirrorimage is said to be chiral any carbon with 4 different substituents will be

a chiral center a pair of nonsuperimposable mirror images are

called a pair of enantiomers


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Optical Isomers of 3-methylhexane


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Plane Polarized Light

light that has been filtered so that only thosewaves traveling in a single plane are allowedthrough


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Optical Activity a pair of enantiomers have all the same physical

properties except one the direction they rotate the plane of plane polarized lighteach will rotate the plane the same amount, but in oppositedirectionsdextrorotatory = rotate to the right

levorotatory = rotate to the left an equimolar mixture of the pair is called a racemic

mixture rotations cancel, so no net rotation


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Chemical Behavior of Enantiomers a pair of enantiomers will have the same

chemical reactivity in a non-chiral environment but in a chiral environment they may exhibit

different behaviorsenzyme selection of one enantiomer of a pair


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Name L ewis Structure

F ormula Boilin Point

Methane C H

H

H

HCH 4 -162C

Ethane C

H

H

H C H

H

H

CH 3CH 3 -89C

Propane CH

H

H

C

H

H

C

H

H

HCH 3CH 2CH 3 -42C

Butane CH

H

H

C

H

H

C

H

H

C

H

H

H CH3CH 2CH 2CH 3 0C

Pentane CHH

H

C

H

H

C

H

H

C

H

H

C

H

H

H CH 3CH 2CH 2CH 2CH 3 36C

Hexane CHH

H

C

H

H

C

H

H

C

H

H

C

H

H

C

H

H

H CH3CH 2CH 2CH 2CH 2CH 3 69C


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Naming

each name consists of 3 parts prefix

indicates position, number, and type of branchesindicates position, number, and type of each functional group

parentindicates the length of the longest carbon chain or ring

suffixindicates the type of hydrocarbon

ane, ene, yne

certain functional groups


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Naming Alkanes1) Find the longest continuous carbon chain

2) Number the chain from end closest to a branchif first branches equal distance use next in

3) Name branches as alkyl groups

locate each branch by preceding its name withthe carbon number on the chain4) List branches alphabetically

do not count n-, sec-, t- , count iso

5) Use prefix if more than one of same group present

di, tri, tetra, penta, hexa

do not count in alphabetizing


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More Alkyl Groups

C C C C

C C C

C

H

H

H

H

H

H

H

H

H

H

H

H

H

H H

C H 3

C H 3

C H 3

H3C

C C CC H 3H

H

H H

H

H

(C H 3)2C H C H 2- , IS OB U T Y L

C H3

C H2

(C H3

)C H - , s e c -B U T Y L

C H 3C H 2C H 2C H 2-, n - B U T Y L

(C H 3)3C - , tert-- B U T Y L


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Examples of Naming Alkanes

2-methylpentane

H H H H H

H C C C C C H

H CH 3 H H H

3-isopropyl-2,2-dimethylhexane

H CH 3 H H H H

H C C C C C C H

H CH 3 CH H H H

CH 3 CH 3


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Example Name the alkane

1) find the longest continuous C chain and use itto determine the base name

CH 3 CHCH 2 CHCH 3

CH 3 CH 3

CH 3CHCH 2CHCH 3

CH 3 CH 3since the longest chain has 5 C

the base name is pentane


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2) identify the substituent branches

CH 3 CHCH 2 CHCH 3

CH 3 CH 3

there are 2 substituents both are 1 C chains, called methyl

CH 3CHCH 2CHCH 3

CH 3 CH 3


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CH 3CHCH 2CHCH 3

CH 3 CH 3


3) number the chain from the end closest to asubstituent branchif first substituents equidistant from end, go to nextsubstituent in

both substituents areequidistant from the end

1 2 3 4 5

2 4

then assign numbers to each substituent basedon the number of the main chain C its attached to


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Practice Name the Following

CH3CHCHCH 2CH3

CH3

CH2CH3


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CH3CHCHCH 2CH3

CH3

CH2CH3

3-ethyl-2-methylpentane


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Drawing Structural Formulas

draw and number the base chain carbonskeleton

add the carbon skeletonsof each substituent on theappropriate main chain C

add in required Hs

4-ethyl-2-methylhexane

C C C CC C

C C C

CH3 CH2 CH2 CH3CH CHCH3 H2C CH 3

C C C C C C1 2 3 4 5 6


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Practice Draw the structural formula of 4-

isopropyl-2-methylheptane


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Practice Draw the structural formula of 4-

isopropyl-2-methylheptane

CH 3 CH 2 CH 2CH CH

CH 3 CH 3HC

CH 3

CH 2 CH 3


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Alkenes also known as olefins aliphatic, unsaturated

C=C double bonds formula for one double bond = C nH2n

subtract 2 H from alkane for each double bond trigonal shape around C

flat

much more reactive than alkanes polyunsaturated = many double bonds


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Alkenes

C CH H

HH

ethene = ethylene

C CH H

CH 3H

propene


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Alkynes

also known as acetylenes aliphatic, unsaturated C C triple bond formula for one triple bond = C nH2n-2

subtract 4 H from alkane for each triple bond

linear shape more reactive than alkenes


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Alkynesethyne = acetylene propyne

C C HH C C CH 3H


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Naming Alkenes and Alkynes

change suffix on main name from -ane to - ene for base name of alkene, or to - yne for the base

name of the alkyne number chain from end closest to multiple bond number in front of main name indicates first

carbon of multiple bond


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Examples of Naming Alkenes

2-methyl-1-pentene

3-isopropyl-2,2-dimethyl-3-hexene

H H H

H C C C C C H

H CH 3 H H H

H CH 3 H H

H C C C C C C H

H CH 3 CH H H H

CH 3 CH 3


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Examples of Naming Alkynes

3-methyl-1-pentyne

4-isopropyl-5,5-dimethyl-2-hexyne

H H H

H C C C C C H

CH 3 H H

H CH 3 H H

H C C C C C C H

H CH 3 CH H

CH 3 CH 3


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Name the Alkene

1)find the longest, continuous C chain thatcontains the double bond and use it to determinethe base name

since the longest chain with the double bond has 6 Cthe base name is hexene

H 3 C CH C

H 2 C CH 3

CH CH 3

H 2 C CH 3


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Name the Alkene


there are 2 substituents

one is a 1 C chain, called methylthe other one is a 2 C chain, called ethyl

H 3 C CH C

H 2 C CH 3

CH CH 3

H 2 C CH 3


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H 3 C CH C

H 2 C CH 3

CH CH 3

H 2 C CH 3

Name the Alkene

3) number the chain from the end closest to thedouble bondthen assign numbers to each substituent basedon the number of the main chain C its attached to

1234

5 6

4

3


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Name the Alkene4) write the name in the following order

1) substituent number of first alphabetical substituent substituent name of first alphabetical substituent

use prefixes to indicate multiple identical substituents2) repeat for other substituents3) number of first C in double bond name of main chain

3 ethyl 4 methyl 2 hexeneH 3 C CH C

H 2 C CH 3

CH CH 3

H 2 C CH 31234

5 6

4

3


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Name the Alkyne1) find the longest, continuous C chain that

contains the triple bond and use it to determinethe base name

since the longest chain with the triple bond has 7 Cthe base name is heptyne

CH3 CH2 CCH CH

CH3 CH3HC

CH3

C CH 3


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Name the Alkyne


there are 2 substituents

one is a 1 C chain, called methylthe other one is called isopropyl

CH3 CH2 CCH CH

CH3 CH

3HC

CH3

C CH 3


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CH2 CCH CH

CH3 CH3HC

CH3

C CH 3CH3

Name the Alkyne

3) number the chain from the end closest to thetriple bondthen assign numbers to each substituent basedon the number of the main chain C its attached to

46

1234567


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Name the Alkyne4) write the name in the following order

1) substituent number of first alphabetical substituent substituent name of first alphabetical substituent

use prefixes to indicate multiple identical substituents2) repeat for other substituents

3) number of first C in double bond name of main chain

4 isopropyl 6 methyl 2 heptyne

CH2 CCH CH

CH3 CH3HC

CH3

C CH3CH3

46

1234567


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H3C C

CH 3

CH 2CH 3

C CH


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Free Rotation Around

C C


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Cis-Trans Isomerism


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Reactions of Hydrocarbons

all hydrocarbons undergo combustion combustion is always exothermic

about 90% of U.S. energy generated by combustion2 CH 3CH 2CH 2CH 3( g ) + 13 O 2( g ) 8 CO 2( g ) + 10 H 2O( g )

CH 3CH=CHCH 3( g ) + 6 O 2( g ) 4 CO 2( g ) + 4 H 2O( g )

2 CH 3C CCH 3( g ) + 11 O 2( g ) 8 CO 2( g ) + 6 H 2O( g )

Oth Alk R ti


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Other Alkane Reactions Substitution

replace H with a halogen atominitiated by addition of energy in the form ofheat or ultraviolet light

to start breaking bondsgenerally get multiple products with multiplesubstitutions

C CH H

H

HH

H

heat orUV light

H ClC CH Cl

H

HH

HCl Cl + H Cl+


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Other Alkene and Alkyne Reactions

Addition reactionsadding a molecule across the multiple bond Hydrogenation = adding H 2

converts unsaturated molecule to saturated

alkene or alkyne + H 2 alkane

Halogenation = adding X 2 Hydrohalogenation = adding HX

HX is polarwhen adding a polar reagent to a double or triplebond, the positive part attaches to the carbon withthe most Hs


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Addition Reactions

H

C C

H H

CH3

Cl2

C C

Cl

Cl

CH3

HH

H

+HC C

H H

CH3

C C

H

H

CH3

HH

H

+ H

2H

C C

H H

CH3

C C

H

Cl

CH3

HH

H

+ + H-Cl -


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Aromatic Hydrocarbons contain benzene ring structure even though they are often drawn with C=C,

they do not behave like alkenes


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Resonance Hybrid

the true structure of benzene is a resonancehybrid of two structures

Naming Monosubstituted


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Naming MonosubstitutedBenzene Derivatives

(name of substituent)benzenehalogen substituent = change ending to o

or name of a common derivative

F

fluorobenzene

CH 2CH 2CH 3

propylbenzene

CH 3 NH 2 OH HC CH 2

toluene aniline phenol styrene


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Naming Disubstituted


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Naming DisubstitutedBenzene Derivatives

alternatively, use relative position prefixortho- = 1,2; meta- = 1,3; para- = 1,4

CH 3

Cl

2-chlorotolueneortho -chlorotoluene

o-chlorotoluene

CH 3

Cl

CH 3

Cl

3-chlorotoluenemeta -chlorotoluene

m-chlorotoluene

4-chlorotoluene para -chlorotoluene

p-chlorotoluene


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F

Cl

Br

Br


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F

Cl

Br

Br

1-chloro-4-fluorobenzene 1,3-dibromobenzeneor meta -dibromobenzene

or m-dibromobenzene


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Polycyclic Aromatic Hydrocarbons

contain multiple benzene rings fused togetherfusing = sharing a common bond


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Reactions of Aromatic Hydrocarbons

most commonly, aromatic hydrocarbonsundergo substitution reactions replacing Hwith another atom or group

Functional Groups


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Functional Groups other organic compounds are hydrocarbons in which

functional groups have been substituted for hydrogens a functional group is a group of atoms that show a

characteristic influence on the properties of themolecule

generally, the reactions that a compound will perform aredetermined by what functional groups it hassince the kind of hydrocarbon chain is irrelevant to thereactions, it may be indicated by the general symbol R

CH 3 OHR group functional group


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Alcohols


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Alcohols R-OH

ethanol = CH 3CH 2OHgrain alcohol = fermentation of sugarsalcoholic beverages

proof number = 2X percentage of alcoholgasohol

isopropyl alcohol = (CH 3)2CHOH2-propanolrubbing alcohol

poisonous

methanol = CH 3OHwood alcohol = thermolysis of wood paint solvent poisonous


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Ald h d Od d Fl


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Aldehyde Odors and Flavors

butanal = butter

vanillin = vanilla

benzaldehyde = almonds

cinnamaldehyde = cinnamon

O

HC CH 2CH 2CH 3

O

C

H

HC

O

C C

H

H

H

OO

HO

HO

Ketone Odors and Flavors


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Ketone Odors and Flavors acetophenone = pistachio

carvone = spearmint

ionone = raspberries

muscone = musk

OC

H3C

O CH 3

O

H3C

C

CH 3

CH 2

CH3

CH3H3C O

C CH 3CCH

H

R i


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Reactions

aldehydes and ketones are generally synthesized by the oxidation of alcohols therefore, reduction of an aldehyde or ketone

results in an alcohol


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Carbonyl Group

C=O group is highly polarmany reactions involve addition across C=O,

with positive part attached to O


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Addition to C=O

C b li A id


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Carboxylic Acids RCOOH sour tasting weak acids citric acid

found in citrus fruit

ethanoic acid = acetic acidvinegar

methanoic acid = formic acidinsect bites and stings

O

OHCH

O

OHCCH 3

OH

O

HO C C

CH2

C

C

O

O

OH

OH

CH2


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Carboxylic Acids

made by the oxidation ofaldehydes and alcoholsOH on the end of the chain

always on main chainhas highest precedence

C of group always C1 position not indicated in name

change ending to oic acid

H3C CH 2

OH

H3C

O

C OHoxidation

ethanoic acidethanol

oxidation

O

CH

O

COH

benzaldehyde benzoic acid

Naming Carboxylic Acids


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Naming Carboxylic Acids

Esters


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Esters

R COO R sweet odor made by reacting carboxylic acid

with an alcoholR aCOOH + R bOH R aCOOR b + H 2O name alkyl group from alcohol, then

acid name with oate ending

precedence over carbonyls, but notcarboxylic acidnumber from end with ester group

O

COH

C CH 3

O

O

aspirin

methyl butanoate

Naming Esters


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Naming Esters

Condensation Reactions


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Condensation Reactions a condensation reaction is any organic reaction

driven by the removal of a small molecule, likewater esters are made by the condensation reaction

between a carboxylic acid and an alcohol the reaction is acid catalyzed

acid anhydrides are made by the condensation

reaction between 2 carboxylic acid molecules the reaction is driven by heat

R C

O

OH OH C

O

R' R C

O

O C

O

R'

+ + HOH

Synthesis of Aspirin


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Synthesis of Aspirin(Acetylsalicylic Acid)

Ethers


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Ethers R O R ether = diethyl ether = CH 3CH 2OCH 2CH 3

anesthetic

to name ethers, name each alkyl groupattached to the O, then add the word ether to the end

diethyl ether


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Amines


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Amines many amines are biologically active

dopamine a neurotransmitterepinephrine an adrenal hormone

pyridoxine vitamin B 6

alkaloids are plant products that arealkaline and biologically active

toxicconiine from hemlockcocaine from coca leavesnicotine from tobacco leavesmescaline from peyote cactusmorphine from opium poppies

HO

HO

CH 2CH 2 NH 2

dopamine

N

N

CH 3

nicotine


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Amine Reactions

weak basesreact with strong acids to form ammonium salts

RNH 2 + HCl RNH 3+Cl react with carboxylic acids in a condensation

reaction to form amides

RCOOH + HNHR RCONHR + H 2O

M l l


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Macromolecules

polymers are very large molecules made byrepeated linking together of small molecules

monomers natural modified natural polymers synthetic

plastics, elastomers (rubber), fabrics, adhesives composites

additives such as graphite, glass, metallic flakes

Nat ral Pol mers


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Natural Polymers

polysaccharidescellulose (cotton)starch

proteins nucleic acids (DNA) natural latex rubber, etc. shellac amber, lignin, pine rosin asphalt, tar

Modified Natural Polymers


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Modified Natural Polymers

Cellulose AcetateRayonfilm

Vulcanized Rubber Gun Cotton Celluloid

ping-pong balls Gutta Percha

fill space for root canal Casein

buttons, mouldings, adhesives


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Addition Polymerization


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monomers add to the growing chain insuch a manner that all the atoms in theoriginal monomer wind up in the chain

no other side products formed, no atomseliminated

first monomer must open to startreaction

done with heat or addition of an initiator chain reactioneach added unit ready to add another



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initiatorC C

H

H

H

ClCl

C CH

H H

H

Cl

C CH

H H

H

+ C C

H

H

H

ClCl

C CH

H H

H Cl

C C

H H

H

Cl

C CH

H H

H Cl

C C

H H

H

+ C C

H

H

H

Cl Cl

C CH

H H

H Cl

C C

H H

H Cl

C C

H H

H

initiatoretc.


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Condensation Polymerization

monomer units are joined by removing smallmolecules from the combining units

polyesters, polyamides lose water no initiator needed chain reaction

each monomer has two reactive ends, so chaincan grow in two directions

Condensation Polymerization


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+ +

+C C

O O

H O O H H O C H 2 C H 2 O H

H C C

O O

O O C H 2 C H 2 O H + H2O

Nylon
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Nylon polyamides

good physical propertiesaffected by moisture very good heat resistance excellent chemical resistance excellent wear resistance nylon 6,6 made by condensing

1,6 hexandiamine, H 2 N (CH 2)6 NH 2, withhexandioic acid, HOOC (CH

2)

4 COOH

( C H2 ) 6 N H C

O

( CH2 ) 4 C

O

H N
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Chemistry chapter 20 LEC