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Figure 1 shows some compounds made from a halogenoalkane - AQA - A-Level Chemistry - Question 1 - 2017 - Paper 2

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Figure 1 shows some compounds made from a halogenoalkane. Figure 1 Compound J Reaction 1 NaOH(aq) CH3CH2CH2Br Reaction 2 NH2 CH3CH2CH2NH2 Reaction 3 ... show full transcript

Worked Solution & Example Answer:Figure 1 shows some compounds made from a halogenoalkane - AQA - A-Level Chemistry - Question 1 - 2017 - Paper 2

Step 1

Draw the displayed formula of compound J.

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Answer

The displayed formula of compound J is:

    H   H   H
    |   |   |
H - C - C - C - Br
    |   |   |
    H   H   H

Step 2

Name the mechanism for Reaction 2 and give an essential condition used to ensure that CH3CH2CH2NH2 is the major product.

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Answer

The mechanism for Reaction 2 is Nucleophilic substitution. An essential condition to ensure that CH3CH2CH2NH2 is the major product is to use excess ammonia (NH2).

Step 3

Calculate the mass, in grams, of CH3CH2CH2NH2 produced from 25.2 g of CH3CH2CH2Br in Reaction 2 assuming a 75.0% yield.

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Answer

To calculate the mass of CH3CH2CH2NH2 produced:

  1. Calculate the moles of CH3CH2CH2Br:

    extMolarmassofCH3CH2CH2Br=25.2extg/mol ext{Molar mass of CH3CH2CH2Br} = 25.2 ext{ g/mol} extMoles=25.2extg123.2extg/mol=0.204extmol ext{Moles} = \frac{25.2 ext{ g}}{123.2 ext{ g/mol}} = 0.204 ext{ mol}
  2. The reaction gives 1:1 molar ratio, so moles of CH3CH2CH2NH2 produced is also 0.204 mol.

  3. Calculate the mass of CH3CH2CH2NH2:

    extMass=extMoles×extMolarmass=0.204extmol×73.13extg/mol=14.9extg ext{Mass} = ext{Moles} \times ext{Molar mass} = 0.204 ext{ mol} \times 73.13 ext{ g/mol} = 14.9 ext{ g}
  4. Considering the yield:

    extActualmass=14.9extg×0.75=11.175extg ext{Actual mass} = 14.9 ext{ g} \times 0.75 = 11.175 ext{ g}

    Hence, the final answer is 11.2 g (to 3 significant figures).

Step 4

When Reaction 2 is carried out under different conditions, a compound with molecular formula C4H13N is produced. Draw the skeletal formula of the compound. Identify the functional group in the compound including its classification.

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Answer

The skeletal formula of the compound C4H13N is:

     H   H
     |   |
H - C - C - C
     |   |   
     H   N - H 
         |  
         H

The functional group in the compound is an amine, which is classified as a tertiary amine.

Step 5

Identify the reagent and conditions used in Reaction 3.

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Answer

The reagent used in Reaction 3 is NaOH (Sodium Hydroxide), typically in ethanol as the solvent.

Step 6

Name and outline a mechanism for Reaction 3.

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Answer

The mechanism for Reaction 3 is Base Elimination. The steps are:

  1. The lone pair on the hydroxide ion acts as a nucleophile and attacks the beta-hydrogen, forming a double bond.
  2. This results in the elimination of a halide ion, producing an alkene.

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