What is the product of the reaction between hex-3-ene and steam?

A.     Hexan-1-ol

B.     Hexan-2-ol

C.     Hexan-3-ol

D.     Hexan-4-ol

C

Applying IUPAC rules, what is the name of \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{2}}}{\text{COOH}}\)?

A.     2,3-dimethylpropanoic acid

B.     Pentanoic acid

C.     3-methylbutanoic acid

D.     2-methylbutanoic acid

C

There were no comments about this question but it is worth noting that over 56% chose answer D. 

Which organic molecule is not a structural isomer of pentan-1-ol?

A.     pentan-2-ol

B.     2-methylpentan-2-ol

C.     2-methylbutan-2-ol

D.     pentan-3-ol

B

In which pair are both compounds secondary?

D

This question could have been better worded but 72% of the candidates chose the correct answer.

Which of the following pairs are members of the same homologous series?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\) and \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHO}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}\) and \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}}\) and \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COOH}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\) and \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHO}}\)

B

Which properties are features of a homologous series?

I.     Same general formula

II.     Similar chemical properties

III.     Gradation in physical properties

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

D

One respondent opined that the word “gradation” is difficult to understand, particularly for students not working in their mother tongue. Whilst other words could have been used, this word was used because it appears in the syllabus.

Some methane gas is burned in a limited supply of oxygen. Which products could form?

I.     C(s)

II.     CO(g)

III.     CO₂(g)

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

D

We recognize that this might be a language problem. “Incomplete combustion” is not the same as “burned in a limited supply of oxygen”. Candidates may also have not read “could” correctly. The correct answer was D. This was the “hardest” question on the paper.

How many structural isomers exist with the formula \({{\text{C}}_{\text{3}}}{{\text{H}}_{\text{5}}}{\text{C}}{{\text{l}}_{\text{3}}}\)?

A.     3

B.     4

C.     5

D.     6

C

What are possible products of the incomplete combustion of propane?

A.     carbon monoxide, hydrogen and carbon

B.     carbon dioxide, carbon and hydrogen

C.     carbon, carbon monoxide and water

D.     carbon dioxide and water only

C

Which equation represents a propagation step in the reaction of methane with bromine?

A.     \({\text{C}}{{\text{H}}_{\text{4}}} \to {\text{C}}{{\text{H}}_{\text{3}}} \bullet  + {\text{H}} \bullet \)

B.     \({\text{C}}{{\text{H}}_{\text{4}}} + {\text{Br}} \bullet  \to {\text{C}}{{\text{H}}_{\text{3}}} \bullet  + {\text{HBr}}\)

C.     \({\text{C}}{{\text{H}}_{\text{4}}} + {\text{Br}} \bullet  \to {\text{C}}{{\text{H}}_{\text{3}}}{\text{Br}} + {\text{H}} \bullet \)

D.     \({\text{C}}{{\text{H}}_{\text{3}}} \bullet  + {\text{Br}} \bullet  \to {\text{C}}{{\text{H}}_{\text{3}}}{\text{Br}}\)

B

Answer C was the most popular distractor, given by nearly a quarter of the candidates. It is a common misconception that a bromine radical can displace a hydrogen radical.

Which species can oxidize ethanol to ethanoic acid?

A.     \({{\text{I}}^ - }\)

B.     Fe

C.     \({{\text{O}}^{2 - }}\)

D.     Acidified \({{\text{K}}_{\text{2}}}{\text{C}}{{\text{r}}_{\text{2}}}{{\text{O}}_{\text{7}}}\)

D

What is the major product of the reaction between HCl and but-2-ene?

A. 1,2-dichlorobutane

B. 2,3-dichlorobutane

C. 1-chlorobutane

D. 2-chlorobutane

D

What is the mechanism for the reaction of propene with iodine in the dark?

A.     electrophilic addition

B.     electrophilic substitution

C.     free radical substitution

D.     nucleophilic substitution

A

What happens when a few drops of bromine water are added to excess hex-1-ene and the mixture is shaken?

I.     The colour of the bromine water disappears.

II.     The organic product formed does not contain any carbon-carbon double bonds.

III.     2-bromohexane is formed.

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

A

Which substance can be polymerized to produce the polymer below?

A.     But-1-ene

B.     But-2-ene

C.     Propene

D.     2-methylpropene

C

Which of the structures below is an aldehyde?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COC}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COOC}}{{\text{H}}_{\text{3}}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH O}}\)

D

There were three G2 comments on this question stating that the wording of the question was ambiguous (e.g. use of the word relatively etc.). This was discussed at Grade Award and for this reason it was decided to remove this question.

Which order is correct when the following substances are arranged in order of increasing boiling point?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CHO}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHO}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CHO}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{3}}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}} < {\text{C}}{{\text{H}}_{\text{3}}}{\text{CHO}}\)

A

One respondent stated that it would be best to write from least reactive to most reactive in both of these questions. However, “increasing” is written in bold in both questions and, also, this type of question has been asked extensively on previous papers and hence candidates would have understood what was asked for explicitly if they had looked at some of the previous examination papers. In the case of Q.13 60% of candidates gave the correct answer and in Q.27, 68% had the question correct.

Which of the following are isomers of pentane?

I.     2-methylpentane

II.     methylbutane

III.     dimethylpropane

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

C

Which compound is not an isomer of hexane?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHCHC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{3}}}{\text{CC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

B

Which steps are involved in the free-radical mechanism of the bromination of ethane in the presence of ultraviolet radiation?

I.     \({{\text{C}}_2}{{\text{H}}_6} + {\text{Br}} \bullet  \to {{\text{C}}_2}{{\text{H}}_5} \bullet  + {\text{HBr}}\)

II.     \({{\text{C}}_2}{{\text{H}}_5} \bullet {\text{B}}{{\text{r}}_2} \to {{\text{C}}_2}{{\text{H}}_5}{\text{Br}} + {\text{Br}} \bullet \)

III.     \({{\text{C}}_2}{{\text{H}}_5} \bullet  + {\text{Br}} \bullet  \to {{\text{C}}_2}{{\text{H}}_5}{\text{Br}}\)

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

D

Which monomer could be used to form a polymer with the following repeating unit?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{Cl}}\)

B.     \({\text{C}}{{\text{H}}_{\text{2}}}{\text{ClC}}{{\text{H}}_{\text{2}}}{\text{Cl}}\)

C.     \({\text{C}}{{\text{H}}_{\text{2}}}{\text{CHCl}}\)

D.     CHClCHCl

C

Which organic product forms in the following reaction?

\[{{\text{(C}}{{\text{H}}_3}{\text{)}}_2}{\text{CHOH}}\xrightarrow[{{\text{reflux}}}]{{{{\text{K}}_2}{\text{C}}{{\text{r}}_2}{{\text{O}}_7}{\text{/}}{{\text{H}}^ + }}}\]

A.     Ethanoic acid

B.     Propanal

C.     Propanone

D.     Propanoic acid

C

Which compound contains a secondary carbon atom?

A.     CH₃CH(Cl)CH(CH₃)₂

B.     (CH₃)₂CHCH₂Cl

C.     (CH₃)₃CCl

D.     CH₃CH₂Cl

A

How many structural isomers of C₆H₁₄ exist?

A. 4

B. 5

C. 6

D. 7

B

Consider the compound \({\text{(C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{)CH=CH(C}}{{\text{H}}_{\text{3}}}{\text{)}}\). Which statements are correct?

I.     A suitable name is pent-2-ene.

II.     The empirical formula is \({\text{C}}{{\text{H}}_{\text{2}}}\).

III.     An isomer of the compound is pentane.

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

A

Three respondents commented on this question. One respondent stated that a 3D structure should not be used here. As previously mentioned in this report, candidates should be encouraged to see a whole range of different representations of structures and in organic chemistry it is especially important that candidates are exposed to 3D representations as part of the overall teaching of organic chemistry. Another respondent stated that it would have been better if statement I. was instead given as a suitable name for the compound is pent-2-ene, which is a fair comment. This was mirrored by another respondent who stated that the molecule drawn is in fact a geometrical isomer and hence E should have been used. Although this is correct, at SL in Topic 10, it is clearly stated that the distinction between cis and trans isomers is not required (TN for AS 10.1.8), so this is the reason why reference was not given to (2E)-pent-2-ene in the question, so the respondent is correct in stating that it would be better if the term IUPAC name was not given for this reason.

Which of these reactions proceeds by a free radical mechanism in the presence of UV light?

A.     C₆H₆ + Cl₂ → C₆H₅Cl + HCl

B.     C₆H₆ + 3H₂ → C₆H₁₂

C.     CH₂CH₂ + HBr → CH₃CH₂Br

D.     CH₃CH₃ + Cl₂ → CH₃CH₂Cl + HCl

D

Which is a tertiary halogenoalkane?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{Br}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{\text{)Cl}}\)

C.     \({\text{C(C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{3}}}{\text{Br}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHClC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C

Which statement is correct about the polymerization of ethene to poly(ethene)?

A.     The polymer is an alkene.

B.     The monomer ethene and the repeating unit have the same empirical formula.

C.     The monomer ethene is less reactive than the polymer.

D.     The polymer contains C−C single and C=C double bonds.

B

Which structural formula represents a secondary halogenoalkane?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHBrC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

B.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{3}}}{\text{CBr}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{{\text{(C}}{{\text{H}}_{\text{2}}}{\text{)}}_{\text{3}}}{\text{Br}}\)

D.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{2}}}{\text{CHC}}{{\text{H}}_{\text{2}}}{\text{Br}}\)

A

What is the order of increasing boiling point?

A.     C₄H₁₀ < CH₃COOH < CH₃CH₂CHO < CH₃CH₂CH₂OH

B.     C₄H₁₀ < CH₃CH₂CHO < CH₃CH₂CH₂OH < CH₃COOH

C.     CH₃COOH < CH₃CH₂CH₂OH< CH₃CH₂CHO < C₄H₁₀

D.     C₄H₁₀ < CH₃CH₂CH₂OH < CH₃CH₂CHO < CH₃COOH

B

What is the organic product of the reaction between 2-chlorobutane and sodium hydroxide solution?

A.     Butan-1-ol

B.     Butan-2-ol

C.     Butanal

D.     Butanone

B

What is the name of the following molecule applying IUPAC rules?

A.     1,1-dimethylbutane

B.     Hexane

C.     2-methylpentane

D.     4-methylpentane

C

Which equation represents the initiation reaction when methane reacts with chlorine in the presence of ultraviolet light?

A.     \({\text{C}}{{\text{H}}_{\text{4}}} \to {\text{C}}{{\text{H}}_{\text{3}}} \bullet  + {\text{H}} \bullet \)

B.     \({\text{C}}{{\text{l}}_2} \to {\text{2Cl}} \bullet \)

C.     \({\text{C}}{{\text{l}}_2} \to {\text{C}}{{\text{l}}^ + } + {\text{C}}{{\text{l}}^ - }\)

D.     \({\text{C}}{{\text{H}}_3} \bullet  + {\text{C}}{{\text{l}}_2} \to {\text{C}}{{\text{H}}_3}{\text{Cl}} + {\text{Cl}} \bullet \)

B

What is the name of the compound with this molecular structure applying IUPAC rules?

A.     1-methylpropanoic acid

B.     2-methylpropanoic acid

C.     2-methylbutanoic acid

D.     3-methylbutanoic acid

C

Which statements about the chlorine free radical are correct?

I.     It has 18 electrons.

II.     It is an uncharged species.

III.     It is formed by homolytic fission.

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

C

B

Which compound can be oxidized when heated with an acidified solution of potassium dichromate(VI)?

A. CH₃C(O)CH₂CH₃

B. CH₃CH₂CH(OH)CH₃

C. (CH₃)₃COH

D. CH₃(CH₂)₂COOH

B

Which conditions are used to convert ethanol to ethanal?

A.     Excess oxidizing agent and reflux

B.     Excess oxidizing agent and distillation

C.     Excess ethanol and reflux

D.     Excess ethanol and distillation

D

What is the name of the alkane shown in the diagram below, applying IUPAC rules?

A.     Hexane

B.     1,1,1-trimethylpropane

C.     Ethylmethylpropane

D.     2,2-dimethylbutane

D

This question was answered correctly by the most candidates (87.72%).

Which compound could be X in the two-stage reaction pathway?

\({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{4}}} \to \) X \( \to {{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{OH}}\)

A.     \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{6}}}\)

B.     \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{3}}}{\text{OH}}\)

C.     \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{5}}}{\text{Br}}\)

D.     \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{4}}}{\text{C}}{{\text{l}}_{\text{2}}}\)

C

What is the product of the oxidation of butan-2-ol?

A.     But-2-ene

B.     Butanoic acid

C.     Butanal

D.     Butanone

D

This proved to be one of the most challenging questions on the paper with a difficulty index of 42%, with more candidates selecting oxidation products from a primary alcohol (B and C) than the correct response. It did however prove to be a very good discriminator with a discrimination index of 0.56.

A

What is the name of \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{3}}}{\text{CCOC}}{{\text{H}}_{\text{3}}}\), applying IUPAC rules?

A.     2,2-dimethylbutan-3-one

B.     3,3-dimethylbutan-2-one

C.     2,2-dimethylbutanal

D.     3,3-dimethylbutanal

B

Which substance is not produced during the combustion of alkanes?

A.     \({\text{C}}{{\text{O}}_{\text{2}}}\)

B.     CO

C.     C

D.     \({{\text{H}}_{\text{2}}}\)

D

Which conditions are required to obtain a good yield of a carboxylic acid when ethanol is oxidized using potassium dichromate(VI), \({{\text{K}}_{\text{2}}}{\text{C}}{{\text{r}}_{\text{2}}}{{\text{O}}_{\text{7}}}{\text{(aq)}}\)?

I.     Add sulfuric acid

II.     Heat the reaction mixture under reflux

III.     Distil the product as the oxidizing agent is added

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

A

One teacher commented on the G2 form that this question required more specific knowledge than was indicated by the syllabus and indeed many candidates found this question challenging, as indicated by the very high number of blank responses and the difficulty index of 33%. The discrimination index of 0.23 showed that it was accessible to many of the better candidates.

Which are structural isomers?

       I.     CH₃CH₂OH and CH₃OCH₃

       II.     HOCH₂CH₃ and CH₃CH₂OH

       III.     CH₃COOH and HCOOCH₃

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

B

What is the IUPAC name for \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{3}}}\)?

A.     1,1-dimethylpropane

B.     2-ethylpropane

C.     2-methylbutane

D.     3-methylbutane

C

Which statement about a homologous series is correct?

A.     Members of the series differ by CH₃.

B.     Members of the series have the same physical properties.

C.     Members of the series have the same empirical formula.

D.     Members of the series have similar chemical properties.

D

Which three compounds can be considered to be a homologous series?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{OH, C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH, C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH, C}}{{\text{H}}_{\text{3}}}{\text{CHO, C}}{{\text{H}}_{\text{3}}}{\text{COOH}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}{\text{, C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH, (C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{3}}}{\text{COH}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH, C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}{\text{, (C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHO}}\)

A

Which type of reaction occurs between an alcohol and a carboxylic acid?

A. Addition

B. Oxidation

C. Esterification

D. Polymerization

C

What is the IUPAC name of the following compound?

A.     2-methylbutane

B.     Ethylpropane

C.     3-methylbutane

D.     Pentane

A

This question provoked a large number of comments on G2 forms, mainly stating that 2-methylbutane should have been given rather than just methylbutane. There is some merit to this although in this case the word methylbutane alone is not ambiguous. Though many were attracted by the incorrect response of 3-methylbutane, a greater number of candidates answered the question correctly and it proved quite a good discriminator, with a discrimination index of 0.41.

Which equations represent the incomplete combustion of methane?

I.     \({\text{C}}{{\text{H}}_4}{\text{(g)}} + {\text{2}}{{\text{O}}_2}{\text{(g)}} \to {\text{C}}{{\text{O}}_2}{\text{(g)}} + {\text{2}}{{\text{H}}_2}{\text{O(g)}}\)

II.     \({\text{C}}{{\text{H}}_4}{\text{(g)}} + {\text{1}}\frac{1}{2}{{\text{O}}_2}{\text{(g)}} \to {\text{CO(g)}} + {\text{2}}{{\text{H}}_2}{\text{O(g)}}\)

III.     \({\text{C}}{{\text{H}}_4}{\text{(g)}} + {{\text{O}}_2}{\text{(g)}} \to {\text{C(s)}} + {\text{2}}{{\text{H}}_2}{\text{O(g)}}\)

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

C

What product is formed when \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}\) is reacted with acidified potassium dichromate(VI)?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COOC}}{{\text{H}}_{\text{3}}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHO}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COOH}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}}\)

D

When bromine water is shaken with a liquid organic compound, it is rapidly decolourized. What can be determined from this test?

A.     The compound is an alcohol.

B.     The compound is an alkane.

C.     The compound is an alkene.

D.     The compound is an iodoalkane.

C

Though it produced a significant number of blank responses, with a difficulty index of 57%, the majority of the candidates answered this question correctly and with a discrimination index of 0.59 it was one of the best discriminators on the paper.

Which of the following statements about alkenes is not correct?

A.     They have reactive double bonds.

B.     They can form addition polymers.

C.     They react mainly by substitution.

D.     They can react with water to form alcohols.

C

Which compound would decolourize bromine water in the dark?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{{\text{(C}}{{\text{H}}_{\text{2}}}{\text{)}}_{\text{4}}}{\text{OH}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHCHC}}{{\text{H}}_{\text{3}}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{{\text{(C}}{{\text{H}}_{\text{2}}}{\text{)}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C

Which monomer is used to form the polymer with the following repeating unit?

A. CH₃CH=CHCH₃ 

B. CH₃CH₂CH=CH₂ 

C. CH₃CH₂CH₂CH₃ 

D. (CH₃)₂C=CH₂

A

Which compound could be formed when CH₃CH₂CH₂OH is heated with acidified potassium dichromate(VI)?

        I.     CH₃CH₂CHO

        II.     CH₃CH₂COOH

        III.     CH₃COCH₃

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

A

Applying IUPAC rules, what is the name of the compound?

A.     1-ethyl-1,3-dimethylbut-2-ene

B.     2-ethyl-4-methylpent-3-ene

C.     2-methyl-4-ethylpent-3-ene

D.     2,4-dimethylhex-2-ene

D

Which compound is an isomer of octane, \({{\text{C}}_{\text{8}}}{{\text{H}}_{{\text{18}}}}\)?

A.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{2}}}{\text{CH(C}}{{\text{H}}_{\text{2}}}{{\text{)}}_{\text{2}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{2}}}\)

B.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{2}}}{\text{CHC}}{{\text{H}}_{\text{2}}}{\text{CHCHC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{{\text{(C}}{{\text{H}}_{\text{2}}}{\text{)}}_{\text{5}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

D.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{2}}}{\text{CH(C}}{{\text{H}}_{\text{2}}}{{\text{)}}_{\text{2}}}{\text{CHCHC}}{{\text{H}}_{\text{3}}}\)

A

There was some concern that this is not on the syllabus. The examiners consider the question to be a fair extension of assessment statement 10.1.5.

Which statement is correct for members of the same homologous series?

A.     They have the same empirical formula and a gradual change in chemical properties.

B.     They have the same empirical formula and a gradual change in physical properties.

C.     They have the same general formula and a gradual change in chemical properties.

D.     They have the same general formula and a gradual change in physical properties.

D

Which compounds belong to the same homologous series?

A.     CHCCH₂CH₃, CHCCH₂CH₂CH₃

B.     CH₃CH₂CH₂CH₂OH, CH₃CH₂OCH₂CH₃

C.     CH₂CHCH₃, CH₃CH₂CH₂CH₃

D.     CH₃COCH₃, CH₃CH₂OCH₃

A

Which molecule contains an ester group?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COOH}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COOC}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{OH}}\)

D.     \({\text{OHCC}}{{\text{H}}_{\text{2}}}{\text{CHO}}\)

B

Which three compounds can be considered to be a homologous series?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{N}}{{\text{H}}_{\text{2}}}\)     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{N}}{{\text{H}}_{\text{2}}}\)     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{N}}{{\text{H}}_{\text{2}}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{N}}{{\text{H}}_{\text{2}}}\)     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(N}}{{\text{H}}_{\text{2}}}{\text{)C}}{{\text{H}}_{\text{3}}}\)     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{(NH)C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C(C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{4}}}\)     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{2}}}{\text{CHC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COOH}}\)     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COOC}}{{\text{H}}_{\text{3}}}\)     \({\text{HCOOC}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

A

Which type of reaction occurs when methanol and propanoic acid react together in the presence of a catalyst?

A. Addition

B. Condensation

C. Redox

D. Neutralization 

B

What is the structural formula of 2,3-dibromo-3-methylhexane?

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHBrCHBrCH(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHBrCBr(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHBrCBr(C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{2}}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CHBrCHBrCH(C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}{{\text{)}}_{\text{2}}}\)

B

What is the function of the ultraviolet light used in the reaction between ethane and bromine?

A.     It causes bromine free radicals to form bromine molecules.

B.     It causes bromide ions to form bromine molecules.

C.     It causes bromine molecules to form bromide ions.

D.     It causes bromine molecules to form bromine free radicals.

D

The structure of a drug used to treat symptoms of Alzheimer’s disease is shown below. Which functional groups are present in this molecule?

A. Hydroxyl and ester 

B. Hydroxide and ether 

C. Hydroxyl and ether 

D. Hydroxide and ester

C

Which functional group is present in paracetamol?

A.     Carboxyl

B.     Amino

C.     Nitrile

D.     Hydroxyl

D

Which alcohols are oxidized by acidified potassium dichromate(VI) solution when heated?

A. I and II only 

B. I and III only 

C. II and III only 

D. I, II and III

A

How many non-cyclic structural isomers exist with the molecular formula \({{\text{C}}_{\text{5}}}{{\text{H}}_{{\text{10}}}}\)?

A.     2

B.     3

C.     4

D.     5

D

Which molecule has a tertiary nitrogen?

A.     (CH₃)₂NH

B.     (C₂H₅)₄N⁺I⁻

C.     C₃H₇N(CH₃)₂

D.     C₆H₅NH₂

C

What is the name of this compound, using IUPAC rules?

A.     1,1-dimethylpropanoic acid

B.     3,3-dimethylpropanoic acid

C.     2-methylbutanoic acid

D.     3-methylbutanoic acid

D

C

Which of the following substances are structural isomers of each other?

I.     \({\text{C}}{{\text{H}}_{\text{3}}}{{\text{(C}}{{\text{H}}_{\text{2}}}{\text{)}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

II.     \({{\text{(C}}{{\text{H}}_{\text{3}}}{\text{)}}_{\text{2}}}{\text{CHC}}{{\text{H}}_{\text{3}}}\)

III.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{CH(C}}{{\text{H}}_{\text{3}}}{\text{)C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

B

For the reaction pathway below, what are the names for the first and second steps?

\[{\text{C}}{{\text{H}}_{\text{2}}}{\text{CHC}}{{\text{H}}_{\text{3}}} \to {\text{C}}{{\text{H}}_{\text{3}}}{\text{CHClC}}{{\text{H}}_{\text{3}}} \to {\text{C}}{{\text{H}}_{\text{3}}}{\text{CHOHC}}{{\text{H}}_{\text{3}}}\]

B

Which statements are correct for the reaction of ethene with bromine in the absence of ultraviolet light?

I.     It is an addition reaction.

II.     The organic product is colourless.

III.     The organic product is saturated.

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

D

One respondent commented that the absence of UV light was not relevant. The condition was mentioned to exclude the possibility of a substitution reaction.

B

From which monomer is this polymer made?

A

Which describes the reaction between a halogen and ethane?

A

What are possible names of a molecule with molecular formula C₄H₁₀O?

        I.     1-Methoxypropane

        II.     2-Methylpropan-2-ol

        III.     Butanal

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

A

Which equation represents a propagation step in the mechanism for the reaction between ethane, \({{\text{C}}_{\text{2}}}{{\text{H}}_{\text{6}}}\), and chlorine, \({\text{C}}{{\text{l}}_{\text{2}}}\), in the presence of sunlight/UV?

A.     \({{\text{C}}_2}{{\text{H}}_6} + {\text{Cl}} \bullet  \to {{\text{C}}_2}{{\text{H}}_5} \bullet  + {\text{HCl}}\)

B.     \({{\text{C}}_2}{{\text{H}}_6} + {\text{Cl}} \bullet  \to {{\text{C}}_2}{{\text{H}}_5}{\text{Cl}} + {\text{H}} \bullet \)

C.     \({\text{C}}{{\text{l}}_{\text{2}}} \to 2{\text{Cl}} \bullet \)

D.     \({{\text{C}}_2}{{\text{H}}_5} \bullet  + {\text{Cl}} \bullet  \to {{\text{C}}_2}{{\text{H}}_5}{\text{Cl}}\)

A

What is the name of the following compound applying IUPAC rules?

A.     1,1,1-trimethylpropane

B.     2,2-dimethylbutane

C.     3,3-dimethylbutane

D.     2-methyl-2-ethylpropane

B

What is the product of the following reaction?

\[{\text{C}}{{\text{H}}_3}{\text{CH(OH)C}}{{\text{H}}_{\text{3}}}\xrightarrow{{{\text{C}}{{\text{r}}_{\text{2}}}{\text{O}}_{\text{7}}^{2 - }/{{\text{H}}^ + }}}\]

A.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COOH}}\)

B.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{COC}}{{\text{H}}_{\text{3}}}\)

C.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{COOH}}\)

D.     \({\text{C}}{{\text{H}}_{\text{3}}}{\text{C}}{{\text{H}}_{\text{2}}}{\text{C}}{{\text{H}}_{\text{3}}}\)

B

One G2 comment stated that there was an overlap between this question and a similar question in P2, which is correct.

What are the functional groups in the aspirin molecule?

\(\begin{gathered} \begin{array}{*{20}{l}} {{\text{I.}}}&{{\text{Ether}}} \\ {{\text{II.}}}&{{\text{Carboxyl}}} \\ {{\text{III.}}}&{{\text{Ester}}} \end{array} \hfill \\ \hfill \\ \end{gathered} \)

A.     I and II only

B.     I and III only

C.     II and III only

D.     I, II and III

C

What is the name of this compound, using IUPAC rules?

A. 3-methylbutan-3-ol

B. 2-ethylpropan-2-ol

C. 2-methylbutan-2-ol

D. 3-methylbutan-2-ol

C