Halogenoalkanes

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Question 16
Medium

Figure 1 outlines a series of reactions starting from 1-bromobutane:

  • Reaction 1: CH3CH2CH2CH2Br→NaOH(aq)Compound X\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br} \xrightarrow{\text{NaOH(aq)}} \text{Compound X}CH3​CH2​CH2​CH2​BrNaOH(aq)​Compound X
  • Reaction 2: CH3CH2CH2CH2Br→NH3CH3CH2CH2CH2NH2\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br} \xrightarrow{\text{NH}_3} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NH}_2CH3​CH2​CH2​CH2​BrNH3​​CH3​CH2​CH2​CH2​NH2​
  • Reaction 3: CH3CH2CH2CH2Br→reagent/conditionsC4H8\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br} \xrightarrow{\text{reagent/conditions}} \text{C}_4\text{H}_8CH3​CH2​CH2​CH2​Brreagent/conditions​C4​H8​
1.

Draw the displayed formula of Compound X.

[1]
2.

Name the mechanism for Reaction 2 and state an essential condition to ensure that the primary amine, CH3CH2CH2CH2NH2\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NH}_2CH3​CH2​CH2​CH2​NH2​, is the major product.

[2]
3.

Calculate the mass, in grams, of CH3CH2CH2CH2NH2\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NH}_2CH3​CH2​CH2​CH2​NH2​ produced from 16.4 g16.4\text{ g}16.4 g of CH3CH2CH2CH2Br\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{Br}CH3​CH2​CH2​CH2​Br in Reaction 2 assuming a 65.0%65.0\%65.0% yield. Give your answer to 3 significant figures. (Relative atomic masses: H=1.0\text{H} = 1.0H=1.0, C=12.0\text{C} = 12.0C=12.0, N=14.0\text{N} = 14.0N=14.0, Br=79.9\text{Br} = 79.9Br=79.9)

[4]
4.

Under different conditions, Reaction 2 can yield a tertiary amine with the molecular formula C12H27N\text{C}_{12}\text{H}_{27}\text{N}C12​H27​N. Draw the skeletal formula of this compound and state its amine classification.

[2]
5.

Identify the reagent and conditions used in Reaction 3.

[2]

Halogenoalkanes Questions

  1. A Level
  2. /Chemistry
  3. /Halogenoalkanes