Spectroscopy Questions - Student Version
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Name: _______________________________________________
Spectroscopy Problems
Date:
Time: 2 hours 39 minutes
Total marks available: 159
Total marks achieved: ______
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Questions
Q1.
The organic product of the reaction between ethanoyl chloride and methylamine has theformula
(Total for question 1 mark!
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Q".
Kits for manufacturing biodiesel from egetable oils and methanol are sold for home use! The reaction which ta"es place may be represented by the following e#uation!
$%a& 'escribe any two of the main ha(ards when carrying out this reaction! )hat precaution would you ta"e to minimise the ris" in each case*
(#!
+a(ard
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,recaution
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+a(ard
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,recaution
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%b& -uggest t$o enironmental benefits of using these "its. despite the associated ris"s!
("!
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(Total for question % marks!
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Q&.,ropanoic acid reacts with methanol to form an ester! The structure of the ester is
(Total for Question 1 mark!
Q#.
)hich of the following methods may be used in a sin'le step to ma"e carbo/ylic acids*
+ydrolysis of an ester with an al"ali!
) 0eaction of acidified potassium manganate%& with an al"ene!
* +ydrolysis of a nitrile with hydrochloric acid!
D 0eaction of an acyl chloride with ammonia!(Total for question 1 mark!
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Q+.
)hich of the following compounds would react with lithium tetrahydridoaluminate %lithium aluminium hydride& and also with phosphorus%& chloride %phosphorus
pentachloride&* +3+2+244+
) +3+24+3
* +3+ ++3
D +2 ++2+24+(Total for question 1 mark!
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Q%.
n the synthesis of an ester. the use of an acyl chloride and an alcohol gies a better yieldthan the use of a carbo/ylic acid and an alcohol!This is because the reaction between
an acyl chloride and an alcohol is an e#uilibrium! ) an acid and an alcohol goes to completion!
* an acid and an alcohol re#uires a catalyst!
D an acyl chloride and an alcohol goes to completion!(Total for question 1 mark!
Q,.
thanal. +3+4. can be conerted by a two6step synthesis into 26hydro/ypropanoic acid!
(Total for question 1 mark!
Q-. thanoic acid. +344+. can be conerted into ethanoyl chloride. +34l. by the action of
phosphorus%& chloride!
) chlorine!
* dilute hydrochloric acid!
D concentrated hydrochloric acid!(Total for question 1 mark!
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Q.
)hich of the following molecules is a methyl ester*
+344+2+3
) +44+3
* +34+2+3
D +34l(Total for question 1 mark!
Q1/.
7n e/ample of a polyester is
%a& The two monomers needed to form this polymer are(1!
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%b& The type of reaction to form this polymer is(1!
addition!
) substitution!
* condensation!
D hydrolysis!(Total for question " marks!
Q11.The following tests can be carried out on organic compounds!
)arm with 2.86dinitrophenylhydra(ine!) )arm with ehlings or ;enedicts solution!* 7dd solid sodium carbonate!D 7dd phosphorus%& chloride. ,l5!%a& )hich test would gie a positie result with propanoic acid but not with propan616ol*
(1!
)
*
D%b& )hich test would gie a positie result with propanoic acid and with propan616ol*
(1!
)
*
D%c& )hich test would gie a positie result with propanal but not withpropanone*
(1!
)
*
D(Total for question & marks!
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Q1".
;utane61.86diol. +4%+2&84+. and ben(ene61.86dicarbo/ylic acid.
+4444+. react to form apolyester!
%a& The repeat unit of the polyester is
(1!
)
*
D
%b& The type of reaction is
(1!
hydrolysis!
) addition!
* substitution!
D condensation!
(Total for question " marks!
Q1&.
7 section of a polymer is shown below! )hich of the following monomers would form this polymer*
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+4+2+24+ and l4+2+24l
) +4+2+24+ and +44+2+244+
* l+2+24l alone
D +4+2+244+ alone
(Total for question 1 mark!
Q1#.
)hich of the following reagents could be used to produce propanamide.
+3+24N2* 7mmonia and 16chloropropane
) 7mmonia and propanoyl chloride
* <ethylamine and 16chloropropane
D <ethylamine and propanoyl chloride(Total for question 1 mark!
Q1+.
n order to ma"e +3+24N++3. you could use
+3+244+3 = N+3 ) +3+24l = +3N+2
* +3+244>Na= = +3N+2
D +3+24N+2 = +3N+2
(Total for question 1 mark!
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Q1%. 7 se#uence of reactions for the production of lactic acid is shown below!
%a& %i& Name the type and mechanism of the reaction in step "!("!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!%ii& )hich t$o substances need to be added to ethanal to carry out the reaction in step "*
("!
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%iii& ?ie the mechanism for the reaction in step ". using curly arrows to show moementsof electron pairs!
(&!
$%i& The product of step " is not optically actie een though it has a chiral carbon atom in its
formula!/plain. by reference to the mechanism. the reason for the lac" of optical actiity!
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%b& )hat reactant. or combination of reactants. is needed to carry out step &0(1!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!%c& %i& )hat is the systematic name of lactic acid*
(1!
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%ii& @actic acid molecules can combine to form a biodegradable polymer. poly%lactic acid& or,@7!
'raw a section of the polymer with t$o units of the polymer chain and showing allbonds!
(1!
%iii& -uggest why ,@7 is biodegradable!
(1! !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!%i& @actic acid can be prepared from ethene as shown in the scheme! @actic acid alsoforms when mil" turns sour!
-uggest one reason why it would be adantageous to ma"e lactic acid from mil" rather thanfrom ethene!
(1!
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Q1,.
This #uestion is about four organic compounds. each containing two carbon atoms!
+3+24+
) +3+4* +344+
D +34l
%a& )hich is o/idi(ed by ammoniacal siler nitrate* (1!
)
*
D %b& )hich has the highest boiling temperature* (1!
)
*
D
%c& A!A1 mol of each compound is heated separately with e/cess acidified sodiumdichromate%&!
)hich compound reduces the largest amount of sodium dichromate%&*(1!
)
*
D
%d& A!A1 mol of each compound is added separately to identical olumes of water! )hichsolution would hae the lowest p+*
(1!
)
*
D
(Total for question # mark
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Q1-.
our organic compounds are:
+34+
) ++4* +44+
D +44+3
%a& )hich of these compounds has a fruity smell*
(1!
)
*
D
%b& A!A1 mol of each compound is added separately to identical olumes of water!)hich solution would hae the lowest p+*
(1!
)
*
D
%c& A!A1 mol of each compound is heated separately with e/cess acidified sodiumdichromate%& solution! )hich compound reduces the largest amount of sodiumdichromate%&*
(1!
)
*
D
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%d& )hich compound has the highest boiling temperature*
(1!
)
*
D
%e& )hich of these compounds can be o/idi(ed by ammoniacal siler nitrate*
(1!
)
* D
(Total for question + marks!
Q1.
The e#uation for the reaction between ethanoic acid and phosphorus%& chloride is +344+ = ,l5 B +34l = ,4l3 = +l
) +344+ = ,l5 B +344l = ,l3 = +l
* +344+ = ,l5 B +34l = ,l3 = +4l
D 2+344+ = ,l5 B %+34&24 = ,l3 = +24 = l2(Total for question 1 mark!
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Q"/.
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-elect from to D the compound that
%a& forms iodoform with iodine in the presence of al"ali!(1!
)
*
D%b& is chiral!
(1!
)
*
D%c& reacts with Tollens reagent!
(1!
)
*
D%d& can be o/idi(ed to form a "etone!
(1!
)
*
D(Total for question # marks!
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Q"1.
)hich of these is not obsered when ethanoyl chloride reacts with water*
<isty fumes gien off!
) The gas gien off turns damp blue litmus paper red!
* The mi/ture gets hot!
D 7 white precipitate forms!
(Total for question 1 mark!
Q"".
This #uestion is about the four organic substances shown below! +3+2+2+2+4) +3+2+2+244+* +34+2+2+3
D +3+2+2+24l )hich substance will
%a& gie a positie result with both ;radys and Tollens reagents*
(1!
)
*
D %b& be formed by the o/idation of a secondary alcohol*
(1!
)
*
D %c& form the most acidic solution when e#ual amounts are each mi/ed with 1AA cm3 of water*
(1!
)
*
D %d& form steamy fumes in the reaction with ,l5*
(1!
)
*
D (Total for question # marks!
Q"&.
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)hich of the following is a redo/ reaction*
thanal reacting with Tollens reagent!
) thanoyl chloride reacting with ammonia!
* thanoic acid reacting with ethanol!
D thanoic acid reacting with sodium hydro/ide!(Total for question 1 mark!
Q"#.
7 flow chart for ma"ing 26hydro/y626methylpropanoic acid from propan626ol is shown below!
%a& %i& ?ie the reagents and conditions for Step 1!
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%ii& ,ropanone is formed in -tep 1!?ie a chemical test to identify the carbonyl group and a further test to show the presence
of the group!or both tests. gie the obserations that you would ma"e!
(#!
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arbonyl group
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group
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%b& %i& n Step ". propanone undergoes an addition reaction with +N in the presence of N> ions!?ie the mechanism for this reaction!
(&!
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%ii& /plain why this reaction would not ta"e place at either a ery low or ery high p+!("!
@ow p+
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!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!+igh p+
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%c& %i& The reaction in Step & forms 26hydro/y626methylpropanoic acid. %+3&2%4+&44+!-uggest the type of reaction occurring in Step &!
(1!
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%ii& /plain why the presence of the alcoholic hydro/yl group cannot be confirmed in theinfrared spectrum of 26hydro/y626methylpropanoic acid!
(1!
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%iii& The hydrogen of the alcohol group in 26hydro/y626methylpropanoic acid can be identifiedby a single pea" in the nmr spectrum!
?ie the chemical shift you would e/pect for this pea"!(1!
!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
%i& +ow many pea"s would you e/pect in a high resolution nmr spectrum for 26hydro/y626methylpropanoic acid. %+3&2%4+&44+*
(1!
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%& /plain why. in high resolution nmr. the pea" due to the hydrogens of the 26methyl groupin 26hydro/y626methylpropanoic acid is a singlet!
(1!
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%i& )ould you e/pect 26hydro/y626methylpropanoic acid to hae optical isomers*Custify your answer!
(1!
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%d& %i& <olecules of 26hydro/y626methylpropanoic acid react together to form a condensationpolymer!
'raw a displayed formula for this polymer. showing two repeating units!("!
%ii& ?ie the name of the functional group that lin"s the two molecules in the polymer!(1!
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(Total for question "/ marks!
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Q"+.
onsider the four compounds shown below!
+344+3
) +344+* +34N++2+3
D +34l
)hich of these compounds
%a& will react most igorously with water*
(1!
)
* D
%b& forms methanol when reflu/ed with a#ueous sodium hydro/ide*
(1!
)
*
D
%c& has at least one triplet in its high resolution proton nmr spectrum*
(1!
)
*
D
(Total for question & marks!
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Q"%.
The spectra of the compounds with the formulae +3+%4+&+3 and +3+2+24+ can bedistinguished by
the alue of m/e of the molecular ion in the mass spectrum!
) the presence of a fragment with m/e D15 in the mass spectrum! * the presence of an absorption pea" due to 4>+ in the infrared spectrum!
D the number of pea"s in the nmr spectrum!(Total for question 1 mark!
Q",.
7n organic compound. . was analy(ed in a laboratory!%a& ompound was found to hae the following percentage composition by mass:
%i& Ese these data to calculate the empirical formula of compound . showing yourwor"ing!
("!
%ii& The mass spectrum of is shown below!
Ese your answer to %a&%i&. and the mass spectrum of . to show that the molecular formulaof compound is 8+F42!("!
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%b& The infrared spectrum of has a broad pea" at appro/imately 35AA cm>1 and a sharppea" at appro/imately 1GAA cm>1! dentify the bond responsible for the pea" at
("!35AA cm>1
1GAA cm>1
%c& %i& -ome chemical information about compound is gien below!
• is a neutral organic compound!
• has no effect on Tollens reagent!
•
turns hot acidified potassium dichromate%& solution from orange to green!)hat does each of these three pieces of information suggest about the nature of *
(#!
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%ii& Ese your answers to parts %b& and %c&%i& to name the two functional groups present in!
(1!
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$%d& The high resolution proton nmr spectrum of is shown below!
The relatie number of protons causing the pea"s shown are: C D 1. K D 1. @ D 3 and < D 3!
Ese the information aboe to determine the structural formula of !
n your answer. you should refer to the number of pea"s. their relatie si(es and theirsplitting patterns!
(,!
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Q"-.This #uestion is about the reactions of butanoic acid. +3+2+244+! t has a foul smell andbehaes li"e a typical carbo/ylic acid!
%a& %i& The addition of sodium carbonate solution is often used as a chemical test to distinguishcarbo/ylic acids. li"e butanoic acid. from other compounds. such as aldehydes!
/plain why old stoc"s of aldehydes often react with sodium carbonate solution!
(1!
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%ii& +ow would the result of this test distinguish between a carbo/ylic acid and an old stoc" of
an aldehyde*(1!
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%iii& )rite the balanced chemical e#uation. including state symbols. for the reaction of sodiumcarbonate solution with butanoic acid!
("!
$%i& nfrared spectroscopy is a good physical method to distinguish carbo/ylic acids from otherorganic compounds! ?ie the waenumbers of t$o characteristic absorptions for a carbo/ylicacid! ndicate the bond responsible for each absorption! -uggest why one of the absorptions isbroad!
(&!
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%& +igh resolution nuclear magnetic resonance spectroscopy is a suitable physical method touse alongside infrared spectroscopy to identify butanoic acid! -tate the total number of pea"sand suggest the splitting pattern for each pea" that you would e/pect for butanoic acid.+3+2+244+!
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%b& -"etch the titration cure obtained when 5A cm3 of A!1A mol dm>3 sodium hydro/ide solutionis added to 25 cm3 of A!1A mol dm>3 butanoic acid!
(#!
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%c& %i& )hat would you see when phosphorus pentachloride. ,l5. reacts with butanoic acid*
(1!
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%ii& ?ie the structural formula and name of the organic product of this reaction!
("!
-tructural formula
Name
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%d& %i& ?ie the name or formula of the organic product of the reaction between butanoic acidand lithium tetrahydridoaluminate %lithium aluminium hydride&!
(1!
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%ii& )ater cannot be used as the solent in this reaction because it reacts with lithiumtetrahydridoaluminate! -uggest a suitable solent!
(1!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
%iii& -tate the type of reaction that ta"es place between butanoic acid and lithiumtetrahydridoaluminate! Custify your classification!
("!
Type
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Custification
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%e& %i& ;utanoic acid can be reacted with methanol to ma"e methyl butanoate! -tate t$o conditions that help to speed up this reaction!
("!
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%ii& 'raw the displayed formula of methyl butanoate!
(1!
%iii& dentify another chemical. by name or formula. which could be added to methanol to ma"emethyl butanoate!
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$%i& ?ie t$o adantages and one disadantage of using the reaction occurring in %e&%iii&.compared to the reaction in %e&%i&. when ma"ing methyl butanoate!
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dvanta'es
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Disadvanta'e
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(Total for Question "- marks!
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Q".
7n organic compound. Q. is found to contain 89!3H carbon and I!FH hydrogen by mass!
%i& Ese these data to confirm its empirical formula is 3+542!
(&!
%ii& The structure of Q is shown below!
The table below summarises some information about parts of the nmr spectrum ofcompound Q!Ese the 'ata ;oo"let. and your "nowledge of splitting patterns. to complete the table withrespect to the features of compound Q shown in bold!
(#!
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Q&/.
This #uestion is about compounds . 8+1A4. and 2. 8+F4!%a& ompound . 8+1A4. can be o/idi(ed to compound 2. 8+F4! The infrared
spectrum of is gien below!
)hat can be deduced about the structures of and 2 using all this information and
the data boo"let* Custify your answer!(#!
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%b& ;elow are the nmr spectra of and 2!
$Ese these nmr spectra and your answer to %a& to deduce the structural formulae of
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and 2! Custify your answer and e/plain why both nmr spectra are consistent with these structures!
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(Total for question 1/ marks!
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Q&1.
The carbo/ylic acid. propanoic acid. can be prepared by o/idation of the alcohol. propan616ol!
%a& %i& dentify a suitable o/idi(ing agent you could use in this reaction!
(1!
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%ii& f you carried out this preparation in the laboratory. describe t$o measures you would ta"e toensure the ma/imum possible yield of propanoic acid is obtained!
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%iii& ,ropanoic acid can be made by the hydrolysis of a nitrile! ?ie the structuralformula of the nitrile and write an e#uation for this reaction!
(&!
-tructural formula
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#uation
$%b& ,ropanoic acid reacts with methanol. +34+. to form the ester. methyl propanoate!
en with the use of a catalyst. this reaction is #uite slow and incomplete! -uggest a reagent. toreplace the propanoic acid. which would form the ester at a faster rate! -uggest t$o reasons why your chosen reagent reacts faster!
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%c& The structure of methyl propanoate can be inestigated by using high resolution1+ nuclear magnetic resonance %nmr& spectroscopy!%i& )hat type of radiation interacts with 1+ nuclei in nmr spectroscopy*
(1!
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%ii& 'escribe what happens to 1+ nuclei when they absorb this radiation!("!
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%iii& omplete the table to show alues for the chemical shift of the different 1+ nuclei in methylpropanoate and their splitting pattern! ,age G of the data boo"let gies information aboutchemical shifts!
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(Total for question 1# marks!
