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35 questions
Chemistry/Paper 1/Organic Synthesis
CAIEAS Level9701-as · Paper 1

Organic Synthesis

35 questions· page 1 of 4

Q342025 Oct/Nov·P111MMedium-Easy

Three mixtures are heated under reflux.

Which mixtures will produce sodium propanoate as one product?

  1. CH3CH2CHO+NaBH4(aq)\text{CH}_3\text{CH}_2\text{CHO} + \text{NaBH}_4(\text{aq})
  2. CH3CH2CH2OH+Na(s)\text{CH}_3\text{CH}_2\text{CH}_2\text{OH} + \text{Na}(\text{s})
  3. CH3CH2CN+NaOH(aq)\text{CH}_3\text{CH}_2\text{CN} + \text{NaOH}(\text{aq})

Options

A   1, 2 and 3
B   1 and 2 only
C   2 and 3 only
D   3 only

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Q342025 Oct/Nov·P121MMedium

An organometallic lithium compound, RLi, contains the nucleophile R\text{R}^-.

CH3CH2Li\text{CH}_3\text{CH}_2\text{Li} reacts with pentan-2-one. The mechanism is nucleophilic addition. The first step produces an anion which is then protonated to form the final product.

Which organic product is formed?

Options

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Q282024 Feb/Mar·P121MMedium-Easy

A sequence of reactions takes place. The major product is compound Z.

What is compound Z?

Options

A   propanone
B   propene
C   propan-1-ol
D   propan-2-ol

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Q302024 Oct/Nov·P121MMedium-Easy

X and Y are the reagents required to convert 1-bromopropane into butanoic acid.

What are the correct identities of reagents X and Y?

Options

XY
ANH3\text{NH}_3HCl(aq)\text{HCl(aq)}
BKCN in C2H5OH\text{KCN in C}_2\text{H}_5\text{OH}NaOH(aq)\text{NaOH(aq)}
CKCN in C2H5OH\text{KCN in C}_2\text{H}_5\text{OH}HCl(aq)\text{HCl(aq)}
DHCN\text{HCN}NaOH(aq)\text{NaOH(aq)}
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Q322024 Oct/Nov·P131MMedium-Easy

When X is added to NaOH(aq)\text{NaOH}(\text{aq}) and heated under reflux, pentan-2-ol is made.

Which organic product is made when X is heated with a solution of KCN dissolved in ethanol?

Options

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Q322023 Oct/Nov·P111MMedium-Easy

Propanoic acid can be made from bromoethane using a two-stage synthesis.

Which pair of reagents is most suitable?

Options

reagent for stage 1reagent for stage 2
Ahydrogen cyanideaqueous sodium hydroxide
Baqueous sodium hydroxideexcess acidified potassium dichromate(VI)
Cethanolic sodium hydroxideacidified potassium manganate(VII)
Dpotassium cyanidedilute hydrochloric acid
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Q332023 Oct/Nov·P121MMedium-Easy

Propanoic acid can be used to make propene by a two-stage synthesis.

Which row shows suitable reagents for this synthesis?

Options

reagent for first stagereagent for second stage
ALiAlH4\text{LiAlH}_4conc. H2SO4\text{H}_2\text{SO}_4
BLiAlH4\text{LiAlH}_4NaOH\text{NaOH} in ethanol
CNaBH4\text{NaBH}_4conc. H2SO4\text{H}_2\text{SO}_4
DNaBH4\text{NaBH}_4NaOH\text{NaOH} in ethanol
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Q322023 Oct/Nov·P131MMedium-Easy

Propanoic acid can be made from bromoethane using a two-stage synthesis.

Which pair of reagents is most suitable?

Options

reagent for stage 1reagent for stage 2
Ahydrogen cyanideaqueous sodium hydroxide
Baqueous sodium hydroxideexcess acidified potassium dichromate(VI)
Cethanolic sodium hydroxideacidified potassium manganate(VII)
Dpotassium cyanidedilute hydrochloric acid
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Q322022 May/Jun·P121MMedium

The structure of coniine is shown.

Coniine can be synthesised by reacting ammonia with a dibromo compound, X.

NH3+C8H16Br2coniine+2HBr\text{NH}_3 + \text{C}_8\text{H}_{16}\text{Br}_2 \rightarrow \text{coniine} + 2\text{HBr}

What is compound X?

Options

A   1,1-dibromo-2-propylcyclopentane
B   1,2-dibromo-2-propylcyclopentane
C   Br(CH2)3CHBr(CH2)3CH3\text{Br(CH}_2)_3\text{CHBr(CH}_2)_3\text{CH}_3
D   Br(CH2)4CHBr(CH2)2CH3\text{Br(CH}_2)_4\text{CHBr(CH}_2)_2\text{CH}_3

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Q382022 May/Jun·P131MMedium

Which compound can be used to make propanoic acid by treatment with a single reagent?

Options

A   CH2=CHCH2CH3\text{CH}_2=\text{CHCH}_2\text{CH}_3
B   CH3CH2CH2CN\text{CH}_3\text{CH}_2\text{CH}_2\text{CN}
C   CH3CH(OH)CN\text{CH}_3\text{CH(OH)CN}
D   CH3CH(OH)CH3\text{CH}_3\text{CH(OH)CH}_3

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