A is CH3CHBrCH2CH3.
- (a)(i)Some reactions of A are shown. [Figure showing reaction scheme] Name A.[1]
- (a)(ii)Name the class of compound to which B belongs.[1]
- (b)There are three structural isomers of A. Draw the structures of these three isomers of A.[2]
- (c)(i)Reaction 1 occurs by two different mechanisms at the same time. These mechanisms are referred to as SN1 and SN2. State what the letters 'S' and 'N' represent in the abbreviation SN1.[1]
- (c)(ii)Complete the SN1 mechanism for reaction 1. Include the structure of the intermediate and all necessary charges, dipoles, lone pairs and curly arrows.[3]
- (d)The SN1 mechanism for reaction 1 is repeated using CH3CHCICH2CH3 or CH₃CHICH2CH3 in place of the CH3CHBrCH2CH3. State and explain how the rates of these two reactions will compare with the rate of the original reaction using CH3CHBrCH2CH3.[3]
- (e)Reaction 2 uses the same reagent as reaction 1, but under different conditions. State two differences in the conditions needed to ensure that reaction 2 is more likely to take place than reaction 1 when this reagent is added.[2]
This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.
Mark scheme
Marking points from the official mark scheme (May/June 2018). The mark or mark type is shown in brackets.
- [1] 2-bromobutane
- [1] ketone
- [2] (CH3)3CBr (structure for 2-bromo-2-methylpropane); (CH3)2CHCH2Br (structure for 1-bromo-2-methylpropane); CH2BrCH2CH2CH3 (structure for 1-bromobutane)
- [1] S = substitution
- [1] N = nucleophilic
- [3] M1 = dipole and curly arrow (for C-Br bond breaking); M2 = intermediate carbocation (H3C-C⁺(H)-CH2CH3, IGNORE CH2CH3 shown as C2H5); M3 = OH⁻ with lone pair and curly arrow from lone pair to the 'C'
- [1] C4H9Cl slower (than C4H9Br)
- [1] C4H9I faster (than C4H9Br)
- [1] C-Cl bond stronger than C–Br OR C–Cl 340 C-Br 280 OR C-I bond weaker then C-Br OR C-Br 280 C-I 240 (1 mark for each point, max 3)
- [1] ethanolic (instead of aqueous)
- [1] hotter/higher temperature (heat under) reflux
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