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13 questions
Chemistry/Paper 2/Organic Synthesis
CAIEAS Level9701-as · Paper 2

Organic Synthesis

13 questions· page 1 of 2

Q5(c)2011 Oct/Nov·P215MMedium-Hard
(c)

In a school or college laboratory, it is possible to convert a sample of hydroxyethanal into aminoethanoic acid in a three-step process.

HOCH2CHOstep 1Xstep 2Ystep 3H2NCH2CO2H\text{HOCH}_2\text{CHO} \xrightarrow{\text{step 1}} \mathbf{X} \xrightarrow{\text{step 2}} \mathbf{Y} \xrightarrow{\text{step 3}} \text{H}_2\text{NCH}_2\text{CO}_2\text{H}

By considering the possible reactions of the functional groups present in hydroxyethanal, you are to deduce a possible route for this conversion.

(i) In the boxes below, draw the structural formulae of your suggested intermediates X and Y.

(ii) State the reagents for each of the three steps you have chosen.

step 1 ......................................................

step 2 ......................................................

step 3 ......................................................

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Q4(a)2010 May/Jun·P217MMedium
(a)

Complete the following reaction scheme which starts with propene.
In each empty box, write the structural formula of the organic compound that would be formed.

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Q5(b)2010 May/Jun·P236MMedium
(b)

Lactic acid may be synthesised from ethanol by the following route.

CH3CH2OHstep 1CH3CHOstep 2CH3CH(OH)CNstep 3CH3CH(OH)CO2H\text{CH}_3\text{CH}_2\text{OH} \xrightarrow{\text{step 1}} \text{CH}_3\text{CHO} \xrightarrow{\text{step 2}} \text{CH}_3\text{CH}(\text{OH})\text{CN} \xrightarrow{\text{step 3}} \text{CH}_3\text{CH}(\text{OH})\text{CO}_2\text{H}

Give the reagent(s) and essential condition(s) for each step.

reagent(s)condition(s)
step 1
step 2
step 3
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Q4(a)2022 Oct/Nov·P218MMedium
(a)

Complete Table 4.1 to:

  • identify a reagent that could distinguish between the compounds in each pair
  • give the positive result of the chemical test and identify which compound shows this result.

Use a different reagent for each test.

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Q1(d)2011 Oct/Nov·P222MMedium
(d)

Compound A is a liquid which does not react with 2,4-dinitrophenylhydrazine reagent or with aqueous bromine.

Suggest two structural formulae for A.

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Q52011 Oct/Nov·P222 partsMedium-Hard
(c)(i)

In the boxes below, draw the structural formulae of your suggested intermediates X and Y.

(c)(ii)

State the reagents for each of the three steps you have chosen.

step 1......................................................

step 2......................................................

step 3......................................................

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Q4(d)2023 Oct/Nov·P213MMedium
(d)

C can be used to form H.

One possible synthesis of H is shown in Fig. 4.5. Different portions of C are used in reactions 1 and 3. Some of the products are then combined to produce H.

Fig. 4.5 does not show any of the inorganic products of the reactions.

Complete Table 4.1 with the reagents and conditions required for each of the reactions shown in Fig. 4.5.

Table 4.1

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Q4(d)2023 Oct/Nov·P233MMedium-Hard
(d)

C can be used to form H.

One possible synthesis of H is shown in Fig. 4.5. Different portions of C are used in reactions 1 and 3. Some of the products are then combined to produce H.

Fig. 4.5 does not show any of the inorganic products of the reactions.

Complete Table 4.1 with the reagents and conditions required for each of the reactions shown in Fig. 4.5.

Table 4.1

reagent and conditions
reaction 1: C → EHBr(g)
reaction 2: E → J
reaction 3: C → G + propanone
reaction 4: J + G → H
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Q32022 Oct/Nov·P222 partsMedium
(c)(iv)

Use the information in 3(c) to suggest a structure for E.

(d)

C2 can be synthesised using A1 as a single organic reactant.

Devise a multi-step synthetic route to form C2 from A1.
Identify relevant reagents and conditions, and state the organic products of each step.

....................................................................................................................................................

....................................................................................................................................................

....................................................................................................................................................

....................................................................................................................................................

....................................................................................................................................................

..............................................................................................................................................

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Q5(b)(i)2023 May/Jun·P231MMedium
(b)(i)

Construct an equation using molecular formulae and [H] for the reaction in Fig. 5.1. Use [H] to represent one atom of hydrogen from the reducing agent.

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