ALCOHOL

The Alcohol Family 1. One of member of homologous series which contain carbon, hydrogen and oxygen. 2. General formula for alcohol is CnH2n+1OH. [n 1,2,!.." !. Alcohol contains the hydroxyl grou#, $O% as their functional grou#. [notes& not hydroxide ion, O%$ , alcohol not is al'aly " (. Alcohol is neutral com#ound. ). Alcohol are named by re#lacing -e for al'ane with ol.

*. +tructural formula and molecule for few alcohol. n ,ame -r -ole'ul Formula +tructural formula % 1 %2 / 2 O% 1 %

12.!. /%!O% 1 -ethanol 1*.1 0 !2 /%(O

% % 12x2 . 1 1 3thanol /2%)O% ) .1* %2 / 2 / 2 O% 2 4ery 0 .1 1 1 im#ortant /2%*O (* % % % % % 1 1 1 % 2 /2 / 2 / 2 O% /!%7O% 1 1 1 % % % /(%9O% /)%11O%

5ro#an$1$ ol

*6

( )

8utan$1$ ol 5entan$1$ ol %exan$1$ ol

7( ::

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/*%1!O%

;& Gi4e names for this alcohol. O% /%! /%2 /% /%2 /%2 /%! Formula& /*%1!O% ,ame & %3<A,$!$O=

Naming Alcohol 1. Find the longest continous carbon chain containing >OH. 2. ,umber the carbon beginning at the end nearer to the > O%, write the number in front of the ending >ol. !. =ocate the al'yl grou# ?branch chain@, gi4e number to the carbon and named the al'yl grou#. 5ut the number in front of the grou#. /%! & methyl /2%) atau /%2/%! & ethyl /!%7 atau /%2/%2/%! & #ro#yl (. /om#lete the name for the alcohol ?ii@ O% /%! /%2 / /%2 /%2 /%! 1 /%! Formula& /7%1)O% ,ame & !$methyl hexan$!$ol

?iii@ O% /%! /%2 /% /% /%2 /%! 1 /%! Formula ,ame & /7%1)O% & ($methyl hexan$!$ol

?iii@ O% /%! /% /% /% /%2 /%2 1 1AA 1 /%! /%! /%! Formula & /9%19O% ,ame & 2, ( > dimethyl he#tan$!$ol

?i4@ / 2% ) O% /%! /%2 /% /%2 /% /%2 B /%! Formula & /9%19O% ,ame & )$ethyl he#tan$!$ol Physical Properties 1. Liqui at room tem#erature. ?#g. *2@ [ no gas" 2. +im#le alcohol are 4ery soluble in water, infinite solubility. -ethanol, ethanol dan #ro#an$1$ol is misci!le in all #ro#ortions ?terlarut cam#ur dengan air dalam semua 'adaran@. The rest of the alcohol less soluble or insoluble. "somerism +imilar to al'enes, isomerism in alcohol results from the branching of the carbon chain and the different location of the hydroxyl grou#. Cou only ha4e to 'now the isomerism in #ro#anol dan butanol. ; & Draw 2 isomers for #ro#anol and ( isomers for butanol, and dan named the isomers.

Propanol

Butanol

Propanol

% % % E E E % B / B / B / B O% E E E % % %

-olecular formula& /!%7O% ,ame& 5ro#an$1$ol

% % % E E E %B/B/B/B% E E E % O% %

-olecular formula& /!%7O% ,ame& 5ro#an$2$ol

Butanol

% % % % E E E E % B / B / B / B / B O% E E E E % % % % % % % % E E E E %B/B/B/B/B% E E E E % % O% %

-olecular formula& /(%9O% ,ame& 8utan$1$ol

-olecular formula& /(%9O% ,ame& 8utan$2$ol

% % % E E E % B / BBB / BBB / B O% E E E % %B/B% % E %

-olecular formula& /(%9O% ,ame& 2$methyl#ro#an$1$ol

% O% % E E E % B / BBB / BBB / B % E E E % %B/B% % E %

-olecular formula& /(%9O% ,ame& 2$methyl#ro#an$2$ol

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#$HANOL 1. 5re#aration of ethanol. i. =aboratory #re#aration ?fermentation@ ii. Fndustrial #roduction ?hydration #rocess@ %a&ing #thanol 'ermentation 1. Two stagesG i. Fermentation ii. 5urification $ through fractional distillation at () oC * !oiling point o+ #$HANOL, 'ermentation o+ -lucose 1. Ceast is added to sugar or starch. 2. Anaero!ic #rocess ? ta'es #lace in the absence of oxygen@. !. Ceast releases enHymes. These enHymes brea' down the sugarsIstarch into glucose, /*%12O*. (. Jymase slowly decom#oses the glucose to form ethanol and carbon dioxide. Jymase 0 /2%)O% 0 /2%*O 2CH/CH2OH *l, + 2CO2 *g, o !6 /

C.H12O. *aq,

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Deli4ery tube /onical flas' 8ea'er Glucose . yeast =ime water

Khen the concentration of ethanol reach 1)L, the yeast dies. ;& %ow to #roduce #ure alcoholM A& 5urified the ethanol through fractional distillation. Puri+ication o+ #thanol 1. 3thanol #roduced from the fermentation #rocess is im#ure, because its mix with the glucose solution. ; & Draw labeled diagram to carry out the #urification of ethanol through fractional distillation #rocess.

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O Thermometer Kater out N =iebig condenser Petort stand with clam# Kater 5roduct from fermentation Kire gauge Pounded conical 5orcelain chi#s 8unsen burner Kater in Distillate ?3thanol@

Fractioning collum

<<<<<<<<<<<<<<<

;& Khy the solutionIfiltrate in rounded conical must heated at 7:o/. A& The boiling #oint of ethanol is 7: o/. ;& 3thanol #roduced may still contains of some water. Khat should be done to be sure that ethanol is 166L #ureM A& Anhydrous calcium oxide or anhydrous calcium chloride is addI#ut into the ethanol.

1!

;& Khat is the function ofG $ thermometer $ #orcelain chi#s $ =iebig condenser A& thermometer is used to ensure that tem#erature is always at 7: o/. 8& 5orcelain chi#s is used to a4oid the solution Qum#edI effer4esence ?brea'ing bubbles@ /& To cooled the ethanol 4a#our to become liRuid. ;& ,amed the #rocess in =iebig condenser. A& /ondensation ;& Khat is the #ro#erties of ethanol A& 5ro#ertiesG $ colourless $ 4olatile $ good organic sol4ent $ miscible with water $ highly flammable $ antise#tic $ chemically reacti4e

1(

;& Khat is the uses of ethanol A& SsesG $ $ $ $ $ $ As a sol4ent in #erfumesIcosmetics As a thinner in 4arnish, in' As a cleaner for com#act disc. As a fuel for trans#ort As a raw material for the manufacture of 4inegar, As a raw material to ma'e industrial #roduct such as antise#tic and cough syru#.

"n ustrial pro uction o+ ethanol 3thene is mix with steam is #assed through concentrate phosphoric aci *catalyst, at /00 oC ?tem#erature@ and .0 atmosphere ?#ressure@. H/PO1 concentrste H2O 555556 /00 o C7 .0 atm

2 C2H1 CH2 4 CH2 +

C2H3OH CH/CH2OH

1)

Chemical Properties 1. Com!ustion i. Alcohol are 4ery flammable sustances. ii. 3thanol burns with non$smo'y and blue flame and releases lot of heat. +uitable for use as fuel, described as clean fuel.

C2H3OH #thanol

/O2 O8ygen

2CO2 + Car!on io8i e

/H2O 9ater

;& Krite combustion eRuation for hexanol C.H1/OH he8anol + :O2 O8ygen .CO2 + Car!on io8i e (H2O 9ater

2. O8i ation i. 3thanol can be oxidised into ethanoic acid by an oxidising agent. [3thanoic acid is a family of carboxilic acids"

CH/CH2OH #tanol

2;O<

CH/COOH + H2O #thanoic aci

1*

;& +how the structural formula for the eRuation abo4e.

% % 1 = % 2 / 2 / 2 O% . 2[O" 1 = % %

% O 1 V % 2 / 2 / 2 O% . %2O 1 %

;& ,amed 2 solutions are commonly used as oxidising agent. ?i@ ?ii@ Acidified #otassium manganate?TFF@, U-nO( ?purple to colourless I decolourised@ Acidified #otassium dichromate?TF@, U2/r2O7 ?orange to green@

;& Draw a labeled diagram for the #rocess.

3thanol . #otassium di'romat?TF@ . dilute sulfuric acid

%eat Distillate ?ethanoic acid@ /old water

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Distillate ?ethanoic acid@ $ /olourless $ Tinegar smell $ 8lue litmus #a#er turns red ?acidic #ro#erties@ /. >ehy ration

$ %2O

A=/O%O=

A=U3,3

1. /on4erted ethanol into ethene and a molecule o+ ?ater. 2. The elimination of water results the formation of a carbon$carbon double bond. !. Dehydration occur when a. ethanol 4a#ours is #assed o4er a heated catalyst such as. i$ 5orous #ot I #orcelain chi#s ii$ 5urnice stone I aluminium oxide, Al2O! Ialumina b. 3thanol is heated under reflux at 176 o/ with excess concentrated sul#huric acid.

/%!/%2O% #thanol

/%2 /%2 #thene

%2O

1:

; & Draw the structural molecule for the #rocess % % 1 1 %2/2/2% 1 1 % O% % % 1 1 % 2 / X / 2 % . % 2O

; & Draw labeled diagram.

Glass wool soa'ed with ethanol

5orcelain chi#s 3thene gas Deli4ery tube Test tube Petort stand with clam#

%eat

%eat

Kater

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