C9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given.

Spectra C 3000 200 180 160 140 120 100 BO 80 B-4-A ppm 4000 3000 2000 8. 10 40 20 11 10 9 7 6 5 3 ppm M 1000 1500 1000 500 Structure: IR: 13C NMR: • Number of types of C: ⚫ Chemical shift(s) of signals: 'H NMR: Number of types of H: Chemical shift(s) of signals: • Integrations: Multiplicity of peaks: Wavenumbers, cm N nonet 0

The primary amine isoamylamine (3-methylbutylamine) occurs naturally in a number of fruits and is used as a food flavouring: (CH3),CHCH,CH,NH, 3-methylbutylamine Suggest two ways in which it can be synthesised from suitable organic precursors. Note that only one of the two methods you propose may involve the reduction of another nitrogen containing compound. In each case, you should indicate what starting material and other reagents are needed, though details of precise experimental conditions or reaction mechanisms are not required.

Propose a structure, carefully outlining how you arrived at that answer

A From the given spectral data, identify the compound and provide justification for MS fragmentation, IR bands and identify the protons and provided NMR data : carbon from the Mol. formula : C5H100 Ms : m/z= 86 · 1, 71, 44 IR (liquid film) : 1728, 2822, 2960 (cm-) 'H-NMR (8) : A =9·75, B =2:32, C =2.21, D =0:98 ppm (suggest splitting pattern) 13 C-NMR (8) : (Proton decoupled) 1 =202.71, 2 = 52.66, 3 = 23-57, 4 = 22·59

Reaction of (CH3)2CO with LiCCH followed by H2O gives compound X, which has a molecular ion in the mass spectrum at 84. It also has prominent absorptions in the IR spectrum at 3600-3200, 3303, 2938, and 2120 cm-1. The proton NMR shows a singlet at 1.53 (6H), a singlet at 2.37 (1H) and a singlet at 2.43 (1H). What is the structure for compound X?