Draw all the isomers (constitutional and stereoisomers) for the molecular formul

Question

Draw all the isomers (constitutional and stereoisomers) for the molecular formula C3H5OCI. There are more than 1 and less than 50 isomers. A couple of points: 10 marks You must draw the structures in line bond. See section 1.2b in your text for a refresher on line bond. Make sure you include all lone pairs and show all hydrogen atoms attached to hetereoatoms and functional groups. For the stereoisomers only, you must show the stereochemistry (dashes and wedges where appropriate). When doing questions like this, you always want to draw the 'best' Lewis structures. That is, if you have a choice between something that has charge separation (formal charges) versus something that has no charge separation (no formal charges) the latter will always win. What I'm saying is that you should only have formal charges when necessary (a nitro group for example). If you really read between the lines I'm telling you that none of your structures should have any formal charges whatsoever.

Explanation / Answer

(COH)(CH2)(CH2Cl) 3-chloropropane (CH3)(CH2)(COCl) Propanoyl chloride (CH3)(CO)(CH2Cl) 1-chloropropanone (CH3(CHCl)(COH) 2-chloropropane got a bit stuck after that. First one O and Cl are at opposite ends, then same end, then next to each other in last two.

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