Wzorowane na: Chemistry HL Paper 2, November 2025, TZ1, pytanie 3(c). Treść, dane i kontekst są zmienione; sprawdzane umiejętności, format i punktacja jak w oryginale.
Informacja do zadań 3b-3g.
Many esters are still known by trivial names. Propyl ethanoate,
Both reactants can be synthesized from alkanes: propan-1-ol from propane via 1-bromopropane, and ethanoic acid from ethane via bromoethane and ethanol. The overall equation for the synthesis of the ester from the two alkanes is
(i) Concentrated sulfuric acid, , is used as the catalyst in the manufacture of propyl ethanoate. Explain how the catalyst affects the reaction.
(ii) The conversion of propane into 1-bromopropane,
begins with an initiation step:
State the condition needed for this initiation step to take place.
(iii) Warming 1-bromopropane with aqueous sodium hydroxide, , converts it into propan-1-ol. Explain the mechanism of this reaction, using curly arrows to show the movement of electron pairs.
(iv) Deduce, for the high-resolution
(i) increases the rate of reaction «and is not used up» ✔
provides an alternative pathway with a lower activation energy / a greater proportion of collisions have energy greater than the activation energy ✔
(ii) ultraviolet light / UV «radiation» ✔
(iii) the lone pair (negative charge) on the oxygen of attacks the carbon bonded to Br, shown by a curly arrow running from that lone pair to the carbon ✔
a second curly arrow runs from the C–Br bond to the Br atom as it leaves ✔
the transition state «in square brackets» carries a negative charge and shows the partial bonds HO···C···Br ✔
forms as the organic product, together with ✔
(iv) Number of signals: 4 ✔
Chemical shift ranges: 0.9–1.0 «ppm, CH3» AND 1.3–1.4 «ppm, middle CH2» AND 3.3–3.7 «ppm, CH2–O» AND 1.0–6.0 «ppm, OH» ✔
Integration traces: 3 AND 2 AND 2 AND 1 ✔
Splitting patterns: triplet «CH3» AND multiplet / sextet «middle CH2» AND triplet «CH2–O» AND «broad» singlet «OH» ✔
(i) M1: increases the rate; M2: lower activation energy through an alternative pathway, or more particles with energy at least equal to the activation energy. (ii) [1] for UV light; accept sunlight or heat; do not accept light alone. (iii) M1: arrow from the nucleophile's lone pair to C; M2: arrow from the C–Br bond to Br (accept it drawn in the transition state); M3: transition state with partial bonds and the negative charge; M4: both products. Award [3 max] for an SN1 mechanism; do not award M3 if a full HO–C bond is drawn in the transition state. (iv) [1] for each line: number of signals, chemical shift ranges, integration, splitting; accept the signals in any order; accept any three correct details for a single signal for [1] each; accept 'multiplet' for the middle CH2.
1-Bromopropane is a primary halogenoalkane, so the concerted SN2 pathway with a single transition state is expected; drawing a carbocation intermediate (SN1) loses one mark.
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