Hydrocarbons Reaction Nomenclature

8/19/2019 Hydrocarbons Reaction Nomenclature

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Hydrocarbons:

Nomenclature and Reactions


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I nternational

U nion of

P ure and

A pplied

C hemistry

IUPAC nomenclaturesystematic nomenclature

“eye-you-pac”

colloquially:


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the alkanes

• Hydrocarbons

• “Paraffins”

• Alkanes: formula CnH2n+2


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he alkanes: table !"2

Methane (CH4)

Ethane (C2H6)

Propane (C3H8)

Butane (C4H10)

Pentane (C5H12)

Hexane (C6H14)

Heptane (C7H16)

Octane (C8H18)

Nonane (CH20)

!ecane (C10H22)

CH4

CH3

CH3

CH3 CH2 CH3

CH3

CH2

CH2

CH3

CH3

CH2

CH2

CH2

CH3

CH3

CH2

CH2

CH2

CH2

CH3

CH3

CH2

CH2

CH2

CH2

CH2

CH3

CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3

CH3

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH3

CH3

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH3


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IUPAC nomenclature of alkanes

1. Find the longest continuous chain of carbon atoms and name it (use linear n

3. Give the substituent a name based on t number of carbon atoms it has. replac -ane ending with -yl

2. umber the chain starting from the endnearest a branch.

!. Give the substituent a numberdetermined on its location on the chain.". #ssemble the

name.

Single sustituent group


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Finding the longest continuousFinding the longest continuous

chainchain

of carbon atoms is not alwaysof carbon atoms is not alwayssimplesimple

$-$-$-$-$-$-$-$-$$-$-$-$-$-$-$-$-$

$

$-$

$-$-$$-$-$

$-$$-$

$$

-$-$-$-$-$$- $-$-$-$-$-$$-$-$-$-$-$

$-$$-$

$-$-$-

$

all possiilitesmust e e!amined

it "on#t al"ays e

the hori$ontal oneas sho"n here

try these also %%&&

''

(( ))


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#ect$ !$!: Common alkyl %rou&s

'C( throu%h C)*: table !"!

Meth"#

Eth"#

Prop"#

But"#

$%oprop"#

$%o&ut"#

(1'Meth"#eth"#)

(2'Meth"#prop"#)

sec 'But"#

(1'Meth"#prop"#)

tert 'But"#

(11'!*eth"#eth"#)

CH3

CH3

CH2

CH3

CH2

CH2

CH3

CH2

CH2

CH2

CH3 CH

CH3

CH3

CH CH2

CH3

CH3

CH2

CH

CH3

CH3

C

CH3

CH3


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CH!

CH2

CH CH!

CH!

Name this alkane

4 3 2 1

2-methylbutane


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CH!

CH2

CH CH!

CH2

CH!

+ind the lon%est continuous

carbon chain 1 2 3

4 5

3-methylpentane


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CH!

CH2

CH CH2

CH2

CH!

CH2

CH2

CH!

,ou must choose the lon%est

continuous carbon chain

4 3 2 1

5 6 7

4-ethylheptane


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-o different substituents• number chain from end closest to a %rou&.

re%ardless of al&habetical order

• locate -here %rou&s are on chain -ith

numbers

• &lace %rou&s in al&habetical order. -ith the

a&&ro&riate number

• assemble the com&lete name. usin% hy&hens

to se&arate numbers from “te/t”


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CH!

CH2

CH2

CH CH CH2

CH!

CH!

CH2

CH!

Number from the end nearest

the first substituent

7 6 5 4 3 2 1

4-ethyl-3-methylheptane


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CH! CH2 CH2 CH CH2 CH CH2 CH!

CH2

CH!

CH!


the first substituent

8 7 6 5 4 3 2 1

3-ethyl-5-methyloctane


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-o or more identical

substituent %rou&s• for t-o identical %rou&s. use &refi/ di -ith the

name of the %rou&: dimethyl. diethyl. etc$

• dimethyl al&habeti0ed as methyl. not dimethyl

• use numbers to locate %rou&s on chain

• use commas to se&arate numbers

• &refi/es: di 1 2 tri 1 ! tetra 1 ) &enta 1


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CH! CH CH CH!

CH!

CH!

3se “di"” -ith t-o substituents

1 2 3 4

2,3-dimethylbutane


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CH! CH2 C CH2 CH2 CH!

CH!

CH!

45ery substituent must %et a

number

1 2 3 4 5 6

3,3-dimethylhexane


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CH!

CH CH2

C CH!

CH!

CH!

CH!

,ou need numbers. e5en thou%h

it a&&ears on the same carbon6

5 4 3 2 1

2,2,4-trimethylpentane


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CH! CH2 CH CH CH2 CH2 CH2 CH2 CH CH!

CH!

CH!

CH!


first substituent

10 9 8 7 6 5 4 3 2 1

2,7,8-trimethyldecane


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CH! CH2 CH CH CH2 CH2 CH2 CH CH2 CH!

CH!

CH!

CH!

Number from the end -hich has

the “first difference”

1 2 3 4 5 6 7 8 9 10

3,4,8-trimethyldecane

N b f th d t


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CH! CH2 CH CH CH2 CH CH2 CH!

CH!

CH!

CH2

CH!


the “first difference”

7imethyl al&habeti0ed as methyl. not dimethyl

1 2 3 4 5 6 7 8

6-ethyl-3,4-dimethyloctane


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8f you can name this.

you can name almost anythin%6

1 2 3 4 5 6

7

8 9

4-isopropyl-2,6,6-trimethylnonane

CH! CH CH2 CH CH2 C CH!

CH!

CH

CH!

CH!

CH!

CH2

CH2 CH!


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he iso&ro&yl %rou& can be named

as a “com&le/” substituent

1-methylethyl

CH!

CH

CH!

2 (


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No-. rename the iso&ro&yl %rou&$

Notice the al&habetical order6

1 2 3 4 5 6

7

8 9

2,6,6-trimethyl-4-1-methylethyl!nonane

CH! CH CH2 CH CH2 C CH!

CH!

CH

CH!

CH!

CH!

CH2

CH2 CH!


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7ecidin% on al&habetical order

for com&le/ %rou&s• Com&le/ %rou&s are al&habeti0ed

under the first letter of the name

• '(.!"dimethylbutyl* 1 d

• '(.(.2"trimethyl&ro&yl* 1 t

• '("ethyl"(.2"dimethylbutyl* 1 e


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Namin% com&le/ substituents ""

this one is a&habeti0ed under d

1,3-dimethylbutyl

C H!

C H C H2

C H

C H!

C H!

) ! 2 (


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Namin% com&le/ substituents

2-ethyl-1,1-dimethylbutyl

CH! C CH CH2 CH!

CH!

CH2

CH!

( 2 ! )


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CH! CH

2 CH

2 CH

2 C CH

2 CH

2 CH

2 CH

!

C

CH2 CH

2 CH

!

CH!

CH2

CH2

CH!

CH!

Name this com&ound6

1 2 3

1 2 3 4 5 6 7 8 9

5-1-ethyl-1-methylpropyl!-5-propylnonane


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CH2CH2

CH2CHCH2

CH!

C CH2CH

2CH!

CH2

CH!

CH!

CCH!

CH!

CH!

Name this t-o -ays "" 'the com&le/

%rou&*

7-1,1-dimethylethyl!-3-ethyl-7-methyldecane

7-tert -butyl-3-ethyl-7-methyldecane


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#ect$ !$: Common names of

alkanes• butane

• isobutane

• &entane

• iso&entane

•neo&entane


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#ect$ !$9: the cycloalkanes

• he names of the cycloalkanes al-ays

contain the &refi/ cyclo

• Cycloalkanes ha5e the %eneral formula

CnH2n


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Cyclic molecules

C"c#opropane

C"c#o&utane

C"c#opentane

C"c#ohexane

CC

C

H H

H

H

H

H

CH2

CH2

CH2

C

C C

C

H

H

H

H

H

H

H

H

CH2

CH2

CH2

CH2

C

C

C

C

C

H HH H

HH

HH

HH

CH2

CH2

CH2

CH2

CH2

C

C

C

C

C

C

H HH

H

H

H

HH

H

H

H

H

CH2

CH2

CH2

CH2

CH2

CH2


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Nomenclature of the substituted

cycloalkanes• 8f there is only one substituent. do not use the “(”$

• 8f there is more than one substituent. you must use all

numbers. includin% “(”6

• Number around the rin% in a direction to %et from thefirst substituent to the second substituent by the shorter

&ath$

• +or eui5alent de%rees of substitution. number in a

direction that follo-s the al&habetical seuence$

• A carbon -ith %reater substitution has &recedence in

numberin%$


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CH!

CH!

1,1-dimethylcyclohexane


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CH!

CH!

CH2CH!

4-ethyl-1,1-dimethylcyclohexane


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$%3

$%3

$%3

$%3$%3

$%2$%3

$%3

$%3

$%3$%2

*+,-dimethylcyclopentane

*-ethyl--methylcyclohe!ane

,-ethyl-*+*-dimethylcycloutane

SomeSome

cycloalkanescycloalkanes

.he more sustituted carontakes precedence e/enthough 0 comes efore 1&

2ra"n

di3erentlyut samename&

4

0 efore 1

* 5

,

*5

,

*

5,*

5

,


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-o -ays of namin% this

1-isopropyl-2-methylcyclohexane

1-methyl-2-1-methylethyl!cyclohexane

CH!

CH

CH!

CH!


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Numberin% starts at the most

hi%hly"substituted carbonCl

CH!

CH!

CH!

2 13 74

6 5

2-chloro-1,1,6-trimethylcycloheptane


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#ect$ !$;: cycloalkyl %rou&s

cyclo&ro&yl cyclobutyl

cyclo&entyl cyclohe/yl


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C

CH!

CH2CH2CH! CH!

3-cyclobutyl-3-methylpentane


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CH

CH2CH

3CH

3

6*-methylpropyl7cyclohe!ane o5-cyclohe!ylutane

8o locant is needed&

9ith one sustituent on a ring + it is automatically on caron *&

*-6*-methylpropyl7cyclohe!ane is o/erkill+ ut ;<

=ings "ith one sustitutent=ings "ith one sustitutent


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Another name of a %rou&

or

Phenyl

or C9H


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CH! CH2 CH CH CH!

CH!

3-methyl-2-phenylpentane


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Sect& ,&): 2egree of Sustitution

methyl methylene

methine

CH!

R R CH2 R

R CH R

R

R C R

R

R

&rimary '(


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CH3 C

CH3

CH3

CH CH2 CH3

CH3

&'#*#*+

,*#*+

*#*+

/$0#*+

# hydrocarbon containing carbon atoms wdiering degrees of substitution

All of the methyl groups 6C>,7 are primary&

0!ample0!ample


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#ect$ !$= "" re5ie-

>e already did this in Cha&ter (

# t ! (? d ! ((


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#ect$ !$(? and !$((:

nomenclature of halides and

nitro com&ounds

fluoro chloro bromo iodo

nitro

Cl @r 8

NA2


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CH ! CH 2 @r

bromoethane "#$%&!

ethyl bromide common!


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@r

bromocyclopropane


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CH! C Cl

CH!

CH!

2-chloro-2-methylpropane "#$%&!tert -butyl chloride common!


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CH! CH CH CH2 CH!

@r CH!

2-bromo-3-methylpentane


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I

iodocyclohexane "#$%&!

cyclohexyl iodide common!


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@r

Cl

1-bromo-2-chlorocyclohexane


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CH! CH CH!

N2

2-nitropropane


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BCAN PR4+8 N #4D #3++8

numbers substituents number "ABE'AN*" endin%

#ect$ !$(2: @lock dia%ram fornomenclature


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CH2 CH2 CH! CH CH2

CH! CH2 CH CH2 CH! CH CH CH!

ethene "#$%&! propene "#$%&!

1-butene 2-butene

ethylene common! propylene common!


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C CH CH!

CH!

CH!

2-methyl-2-butene


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CH! CH CH2 CH2 CH CH CH!

CH!

6-methyl-2-heptene


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CH! CH!

4,4-dimethylcyclohexene


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CH!

2-methyl-1,3-cyclohexadiene


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CH2 CH!

CH2

CH!

2,5-diethyl-1,3-cyclooctadiene


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Fery im&ortant6

benene"t is never cyclohexatriene


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#ect$ !$(): nomenclature of

alkynes• similar system used as -ith alkenes

• endin% is yne

• identify the lon%est chain -ith the tri&lebond

• e5erythin% else is the same as alkenes


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H C C H CH! C C H

CH! CH2 C CH CH! C C CH!

ethyne propyne

1-butyne 2-butyne

*acetylene+


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A?;@80S 6 -@80 7A?;@80S 6 -@80 7

C CC>, C>5C>5C>,

CC>, C C>

C>,

C>,

5-he!yne

-methyl-5-pentyne

.he su! hasprecedence

o/er anysustituents

.he functional group has precedence in numering&

functional

group


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CH! C C

CH!

Cl

C CH!

CH! CH C

CH!

C CH CH2

@r

CH!

4-chloro-4-methyl-2-pentyne

5-bromo-2-methyl-3-heptyne

ene /s yne: "hich one "insBene /s yne: "hich one "insB


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8umer from the end closest to either the doule

ondor the triple ond+ "hiche/er is closest to the end&

ene /s& yne: "hich one "insBene /s& yne: "hich one "insB

C>,-C>5-C C-C>5-C>4C>-C>,5-octen--yne

) D ( , 5 *

Compounds are named: en-yne&

optional but recommended


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C1PU.0= P=E=A1

““=EA8IC 8108C?A.U=0”=EA8IC 8108C?A.U=0”

A/ailale in ChemistryComputer ?a - CF5)G

Eo to ChemApps Holder :

optional, but recommended …..

then choose rst and then Organic

Nomenclature

Chem Apps

Organic


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#ect$ !$(: &hysical

&ro&erties of hydrocarbons• the lon%er the strai%ht chain. the hi%her

the boilin% &oint "" 5an der >aals forces

• isomers that are branched ha5e lo-erboilin% &oints

• hydro%en bondin% increases boilin%

&oints• 7i&ole"di&ole attractions increase b$&$


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#ect$ !$(9: Combustion of

alkanesCnH2n+2 + * O2 n CO2 + (2n+2),2 H2O

-here n 1 number of carbons

+ HE-.///

Exa*p#e0

2 C6H14 + 1 O2 12 CO2 + 14 H2O

#ect ! (;: Halo%enation of Alkanes


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li%ht+ +R H Cl Cl R Cl H Cl

chlorination

e!amples

C> J Cl5 C>,Cl J >Cl

C>,C>5C>, J Cl5 C>,C>C>, J >Cl

Cl

J C>,C>5C>5-Cltakes place at a reneryor a chemical plant - noteasy to do in the la

free-radicalsustitution

reaction

#ect$ !$(;: Halo%enation of Alkanes

.he pre/ious e!amples gi/en.he pre/ious e!amples gi/en


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.he pre/ious e!amples gi/en .he pre/ious e!amples gi/en

assumedassumed

monochlorinationmonochlorination6one chlorine added76one chlorine added7

FU. %the reaction can repeat itself C118 8A10S

C> J Cl5 C>,Cl J >Clmethyl chloride

C>,Cl J Cl5 C>5Cl5 J >Cl methylene chloride

C>5Cl5 J Cl5 C>Cl, J >Clchloroform

C>Cl, J Cl5 CCl J >Clcaron tetrachloride

fully chlorinated product9hat are theIUPAC names B

h i i i i d


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.he reaction must e initiated

It does not occur in the dark&0!posure to ultra/iolet light 6sunlight7 "ill startthe reaction&

>eat "ill also start the reaction&nce reaction starts+ it is e!othermic and continuesalmost e!plosi/ely&

.he rst step is the dissociation ofchlorine :

Cl-Cl 5 Cl&&

&&

&&

&&

&&

&&: : :&h

or

chlorineatoms

diatomic molecule

6radicals7

A t ti f h d tAstraction of hydrogen atom


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Astraction of hydrogen atomAstraction of hydrogen atom

Cl&& :&&&

F@ A C>?=I80 “H=00 =A2ICA?” 6A.17

J

C & >-Cl&& :&&J

Chlorine takes thehydrogen and oneof its electrons

unpaired electron4 “free” radical

>@2=E08 AFS.=AC.I8&&C >

1echanism of chlorination of methane1echanism of chlorination of methane


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C# C#

li%ht2 0 C#

11

11 1

CH3

H + 0 C#11

111

11

0

11H C# + 1 CH

3

1 CH3

+

11

11

11

11

0 0C# C#

11

110CH

3 C# + 0 C#

11

111

11

11

11

110 0

($ 8nitiation

2$ Chain Pro&a%ation 'first ste&*

!$ Chain Pro&a%ation 'second ste&*

a free radical

methyl radical

feeds back intoste& t-o

=0P0A

. I8E

S .0PS

1echanism of chlorination of methaneC>AI8 =0AC.I8

“hydrogen astraction”

“dissociation”


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)$ ermination #te&s

C# C#2 0 C#

11

11

1

1 CH3

CH3

11

11

11

110 0

1 + CH3CH3

0 C#

11

11

1 1 CH3+ 0 C#11 CH3

11

hese ste&s sto&

the chain reaction

“recominations”

1onochlorination of propane:1onochlorination of propane:


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C>,C>5C>, J Cl5 C>,C>C>,Cl

J C>,C>5C>5-Cllimited amount

KU0S.I8

A F

9>A. A=0 .>0 =0?A.IL0 A1U8.S H A A82 F B

IS I. S.A.IS.ICA? 6 5 : ( 7 4 6* : , 7 B

20S S10.>I8E 0?S0 C8.=? .>0 U.C10 B

1onochlorination of propane:1onochlorination of propane:

2oes one isomer predominateB2oes one isomer predominateB

1onochlorination of propane1onochlorination of propane


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C>,C>C>,Cl

C>,C>5C>5-Cl

A F

S.A.IS.ICA? P=02IC.I8 5 M D MC>,-C>5-C>, 4 ( : 5 or ,:*

S.A.IS.ICA? L0=SUS 0NP0=I108.A? =0SU?.S

AC.UA??@ HU82 G M G M

0qualamounts

0qualamounts

perimental results


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perimental resultsshow4

Secondary hydrogens are energenically moreeasily remo/ed than primary hydrogens

C>,C>C>,>

C>,C>5C>,

Secondary >

Primary >

more reacti/e hydrogen


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/tability of freeradicals eplains

results5

H!C C CH!

H

secondary radical

More stable and

easier to form!

H!C CH2 C

H

H

primary radical

Less stable and harder

to form


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/tability of radicals4 *#*+ 6 /$0#*+ 6,*#*+

H!C C CH!

H

secondary radical

less stable thantertiary but morestable than primary

H!C CH2 C

H

H

primary radical

Least stable andhardest to form

H!C C CH!

CH!

tertiary radical

Most stable andeasiest to form!

Hydrocarbons Reaction Nomenclature

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