Wzorowane na: Chemistry HL Paper 2, May 2025, TZ1, pytanie 8(b). Treść, dane i kontekst są zmienione; sprawdzane umiejętności, format i punktacja jak w oryginale.
Informacja do zadań 8a-8f.
Many everyday materials, flavourings and fuels are organic compounds.
The compound X shown below occurs naturally in cocoa and coffee and is used as a flavouring agent.
(i) State the name of the functional group found in compound X.
(ii) Deduce the IUPAC name of X.
(iii) Deduce how many signals the NMR spectrum of X contains and the ratio of their areas (integration traces).
Number of signals:
Relative areas:
(iv) Draw a structural isomer of X taken from a different homologous series.
(v) X can be both oxidized and reduced. Representing X as RCHO, deduce the formula of the organic product formed with an oxidizing agent and the formula of the organic product formed with a reducing agent.
Product of reaction with oxidizing agent:
Product of reaction with reducing agent:
(i) carbonyl ✔
(ii) 2-methylbutanal ✔
(iii) Number of signals: 5 ✔
Relative areas: 3 : 2 : 1 : 3 : 1 « of the ethyl group, , , on C2, » ✔
(iv) any ketone with the molecular formula , e.g. pentan-2-one
OR
an unsaturated alcohol or ether, or a cyclic alcohol or ether, with the molecular formula «e.g. pent-4-en-1-ol, cyclopentanol»
(v) Product of reaction with oxidizing agent: RCOOH ✔
Product of reaction with reducing agent: ✔
(i) [1]; do not accept aldehyde (the class of compound, not the functional group). (ii) [1]; a missing hyphen is not penalized. (iii) M1: five signals; M2: the ratio in any order. (iv) [1] for any correct structure with the formula C5H10O that is not an aldehyde. (v) [1] per product; award [1 max] if the two products are reversed; accept full structures «2-methylbutanoic acid and 2-methylbutan-1-ol».
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