The Student Room Group

EZ isomerism

Can someone explain why the answer is B please

Reply 1

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Reply 2

Addition polymerisation partially breaks the C=C double bond so there is no longer restricted rotation. Try drawing the E-isomer and its repeating unit, and you will notice how the Cl will be able to rotate to appear the same as the repeating unit of the Z-isomer...

Reply 3

Bit late, but you do have an alternative approach - spot the wrong answers and use the process of elimination.

A is wrong, because the positioning of the groups in a given molecule affects how much contact the molecules have with each other. Therefore, the london dispersion forces between the molecules for different geometric isomers are not of the same strengths, hence they have different melting and boiling points.

C is problematic, since you are expected to know that the region described is the fingerprint region and each molecule (and incidentally each geometric isomer) has a uniquely shaped pattern in this region.

D is not correct, as molecular ion peaks don’t just have an associated m/z value. You also have to take into account the intensities of the peaks. Since the molecular ions themselves will have near-identical structures to their parent alkenes, you can argue that the respective molecular ions must be different to each other as the groups are locked in place by the C=C bond with limited rotation. This means the molecular ions formed in each case are not the same and therefore not equally stable, so the intensities of the M^+ peaks will not be the same.
(edited 8 months ago)

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