Give the IUPAC name of CH3CH2CH2CH2CH(OH)CN and describe why the formation of this molecule creates 2 enantiomers.

The IUPAC name of CH3CH2CH2CH2CH(OH)CN is 2-Hydroxyhexanenitrile as its carbon chain is 6 carbons long (Hex). The nitrile group takes naming priority over the alcohol group so goes at the end of the name while the OH group is put at the start of the name (2-Hydroxy) - it is on the 2nd carbon starting from the carbon involved in the nitrile group. DO NOT forget it is hexanenitrile and not hexannitrile - this is an exception to the rule that the 'e' at the end of the carbon chain is dropped. The molecule is saturated so it is -ane and not -ene.This molecule can exist in 2 enantiomers as the nitrile group attacks the planar carbocation during it's formation so a chiral centre is formed which leads to the possibility of stereo-isomerism and therefore 2 non-superimposable mirror image molecules (enantiomers) .

Answered by Owen R. Chemistry tutor

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