By Charles Went (auth.)

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2 Decide whether each of the following species could behave as (1) an electrophile, (2) a nucleophile (3) both, or (d) neither. /CH 3 (3) CH 2 =C "'- CH 3 /CH 3 e l / CH3 (b) CH3 -CH "'(c) CH3 -C "'CH, CH, el •• (f) CH 3 -N==N e.. / CH 3 (d) CH3 -C "'CH 3 .. =N=? (h) CH 3C=N STRUCTURE AND TERMINOLOGY OF SOME COMMON ORGANIC INTERMEDIATES For a hypothetical derivative of methane, CH 3 sociations are theoretically possible - X, the following dis- (1) Heterolysis CH 3 or -0x CH 3 Ell + C~ X CH 3 9 + j(9 xEIl and (2) Homolysis $ ..

If benzene was simply cyclohexatriene, we should expect two different bond lengths, 154 pm and 134 pm, for each of the three single and double bonds 36 ~154pm 0 - - 1 3 4 pm ©-'11139 pm benzene cyclohexatriene The fact that all the bonds are the same, and the bond length is intermediate between that of a single and double bond, is strong support for the postulated resonance structure. (b) Bond lengths in ethanamide The 'expected' and observed bond lengths in ethanamide are as follows 122 pm ~o:: CH 3 -C }' NH2 147pm expected values in classical structure observed values in the real structure The carbon-oxygen bond is longer (128 pm) than a normal carbonyl double bond in an aldehyde or ketone (122 pm).

Eventually, the compound absorbs in the visible region (about 400-750 nm) and so becomes coloured. An interesting example is the molecule of /3-carotene, whose structure has 11 conjugated double bonds H H CH3 H H CH 3 This compound has a very intense absorption at Amax = 450 nm and is responsible for the orange colour of carrots. Infrared spectra The individual atoms in a molecule are not still, but are in a constant state of vibration. This results in stretching, twisting and bending motions in the constituent bonds.

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