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8 Carboxylic acids and their derivatives


Answers to Topic 8 Test yourself questions

1 Hexanoic acid, CH3CH2CH2CH2CH2COOH; octanoic acid CH3CH2CH2CH2CH2CH2CH2COOH; decanoic acid CH3CH2CH2CH2CH2CH2CH2CH2CH2COOH. 2 C3H6O2, CH3CH2COOH, propanoic acid c) CH3CH2CH2COOH(aq) * 'H3(aq) CH3CH2CH2COO'H+(aq) he product is ammonium "utanoate. .odium ethanoate is a salt. here is ionic "onding "etween sodium ions and ethanoate ions. Ionic "onding is strong "onding. /thanoic acid is molecular. he "onds "etween molecules are intermolecular forces0 h!drogen "onds and 1ondon forces. hese are much wea,er than ionic "onds. a) H3C6H2O3(aq) * 3'aOH(aq) 'a3C6H2O3(aq) * 3H2O(aq) b) 4 measured sample of a fruit 5uice could "e titrated with a standard solution of a strong al,ali such as sodium h!droxide. %henolphthalein could "e used for this titration of wea, acids with a strong "ase. .ince fruit 5uices are not clear and colourless, it might "e "etter to follow the titration with a pH meter rather than an acid6"ase indicator. he result could "e used to calculate the total acidit! of the fruit 5uice "ut it could not measure onl! the citric acid concentrations. 7rape 5uice, for example, contains tartaric acid and malic acid as well as citric acid. 4pple 5uice also contains a significant amount of malic acid. a) CH3CH2CH2CH2OH, "utan#8#ol b) CH3CH2COCl, propano!l chloride a) he reaction is rapid at room temperature and gi$es off h!drogen chloride which fumes in moist air. he test indicates the presence of OH groups, which is the reason that alcohols also gi$e a positi$e result. b) 4queous solution of alcohols are neutral. 4queous solutions of car"ox!lic acids ha$e a pH around 36+ and react with a solution of
1 of 3 % &' (ill and A' (unt 2$$# )dexcel Che*istry for A2

4 a) In aqueous solution there is a large excess of water molecules. his means that h!drogen "onding "! ethanoic acid molecules is largel! with water molecules. In a non#polar sol$ent the acid molecules can onl! form h!drogen "onds with each other. b)


%entanoic acid, CH3CH2CH2CH2COOH &utanoic acid, CH3CH2CH2COOH %ropanoic acid, CH3CH2COOH CH3C'(l) * 2H2O(l) * HCl(aq) CH3COOH(aq) * 'H+Cl(aq) b) CH3C'(l) * H2O(l) * 'aOH(aq) CH3COO'a(aq) * 'H3(aq) " H!drol!sis of a nitrile with al,ali produces the salt of the acid. his is ionic and not $olatile. Car"ox!lic acids are wea, acids, and so acidif!ing the solution of the salt with a strong acid con$erts the anion of the acid in the salt to the molecular acid. 8 a) CH3COOH(aq) * -OH(aq) CH3COO-(aq) * H2O(l) he product is potassium ethanoate. b) 2CH3CH2COOH(aq) * 'a2CO3(aq) 2CH3CH2COO'a(aq) * CO2(g) * H2O(l) he product is sodium propanoate. a) b) c) ! a)

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8 Carboxylic acids and their derivatives

18 /th!l ethanoate is a larger molecule than either ethanol or ethanoic acid; it has a permanent dipole "ut no 6OH groups so molecules of the ester cannot form h!drogen "onds with each other. H!drogen "onding is stronger than the attraction "etween permanent dipoles. /thanol and ethanoic acid molecules are "oth held together "! h!drogen "onding. .o ethanol has a higher "oiling temperature than might "e expected from its molecular si;e. 4n ethanoic acid molecule can form more h!drogen "onds than an ethanol molecule. 1# a) %ropan#8#ol and "utanoic acid b) /thanol and sodium methanoate 2$ a) /xcess of dilute acid so that there is plent! of water. b) o ma,e the ester no water is added and the acid is concentrated. 21 .aturated0 palmitic and stearic; 9nsaturated0 oleic and linoleic 22



1! 1"

sodium car"onate to gi$e car"on dioxide gas with effer$escence. + 9sing an excess of one reactant0 adding more of one reactant forces the equili"rium to the right, increasing the proportion of the other (more $alua"le) reactant con$erted to the ester. + 9sing more concentrated sulfuric acid than is needed for its catal!tic effect0 sulfuric acid is a deh!drating agent so it remo$es water (one of the products) from the reaction mixture; this shifts the equili"rium to the right. + :istilling off the product at formed0 this remo$es the ester (the other product) from the reaction mixture, also shifting the equili"rium to the right. CH3COCl(l) * H2O(l) CH3COOH(l) * HCl(g) he car"on6chlorine "ond is "ro,en "! reaction with water. CH3COCl(l) * 2'H3(aq) CH3CO'H2(aq) * 'H+Cl(aq) he second mole of ammonia reacts with h!drogen chloride formed in the reaction to produce ammonium chloride. CH3CH2CO'HCH2CH2CH2CH3, '#"ut!lpropanamide a)

23 4l,aline h!drol!sis is not re$ersi"le and goes to completion. 4lso, using al,ali produces the salt of the fatt! acid which is the soap. 24 .tearic acid, octadecanoic acid 2 a)

prop!l "utanoate b) trans#octadec#<#enoic acid (elaidic acid)

meth!l ethanoate c)

"ut!l ethanoate

2 of 3 % &' (ill and A' (unt 2$$# )dexcel Che*istry for A2

8 Carboxylic acids and their derivatives

than diesel fuel. he reaction with methanol produces separate smaller molecules so that the "iodiesel is more free#flowing and so easier to use as a fuel without ha$ing to modif! engines. If there is moisture present with the al,ali the result is h!drol!sis to form the sodium salts of fatt! acids instead of meth!l esters. >a,ing "iodiesel0 the trigl!ceride reacts with an alcohol such as methanol to produce meth!l esters of fatt! acids and gl!cerol. =aising melting temperature of oils0 trigl!cerides react with each other leading to an exchange of fatt! acids "etween the molecules. a) ?hen "iodiesel "urns it gi$es out a"out the same amount of car"on dioxide as the car"on dioxide ta,en in as the $egeta"le oil formed when the plants grew. b) Car"on dioxide is gi$en out during the manufacture of fertilisers, plant culti$ation, har$esting, extraction of oil and processing of the oil into fuel. @egeta"le oils and corn starch are used to ma,e food. 9sing them to ma,e "iodiesel leads to food shortages and an increase in food prices. 9sing waste plant material, such as straw, means that the manufacture of "iodiesel does not compete with the production of food.

cis#octadec#<#enoic acid (oleic acid) b) 'ormall! the isomers are distinct "ecause the molecules cannot rotate around a dou"le "ond. =otation must somehow "ecome possi"le in the presence of the catal!st for h!drogenation. c) he trans isomer is a linear molecule li,e a saturated fatt! acid. his means that trigl!cerides with elaidic acid can pac, more closel! together with stronger intermolecular forces. 2!




2" a) .odium methoxide is made using sodium (a $er! reacti$e metal) and methanol (a highl! flamma"le liquid). he compound is a $er! strong "ase. b) .odium methoxide is rapidl! h!drol!sed "! water. he methoxide ion is a strong "ase and reacts with water to form methanol and h!droxide ions. 28 he relati$el! large molecules in $egeta"le oil ma,e it more $iscous


3 of 3 % &' (ill and A' (unt 2$$# )dexcel Che*istry for A2