Isomers with molecular formula C₄H₇Cl

Question

What are the possible isomeric structures of chlorobutene $(\ce{C4H7Cl})?$

I've come up with seven:

Wolfram Alpha can find the isomers of a given formula, quite nicely as well. — Ali Caglayan, Feb 20, 2016 at 20:09
@AliCaglayan Quite nicely except that it misses two of them? (2 and 3 from orthocresol's figure in my answer) I assume that it is simply extracting from a database except that surely 1-Chloro-1-methylcyclopropane is in any reasonable db? Weird. — gilleain, Feb 21, 2016 at 9:51
@gilleain I am having a hard time finding any literature on 1-Chloro-1-methylcyclopropane or 1-Chloro-2-methylcyclopropane which might mean that WA has not included it because there is no data on it? — Ali Caglayan, Feb 24, 2016 at 13:18

orthocresol · Accepted Answer · 2016-02-20 14:54:01Z

11

There are 12 different constitutional isomers:

There is also the further possibility of stereoisomerism in some of the compounds above.

3: Two diastereomers (cis- and trans-) are possible.
7, 8, 9: Geometrical isomerism is possible in these alkenes.
11: C-3 (the carbon with the chlorine) is a chiral centre, which leads to two possible enantiomers.

That makes a total of 17 possible isomers.

orthocresol

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answered Feb 20, 2016 at 11:20

gilleain

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2

$\begingroup$ And that's not counting the cis/trans things. $\endgroup$
– Ivan Neretin
Feb 20, 2016 at 12:33
$\begingroup$ I hope I didn't miss anything out. $\endgroup$
– orthocresol
Feb 20, 2016 at 14:54
$\begingroup$ @orthocresol much better answer than mine! Should be a way to transfer answers, I guess. Thanks $\endgroup$
– gilleain
Feb 20, 2016 at 15:02
$\begingroup$ Well, you did the work finding the 12 constitutional isomers, I just touched it up a bit :) $\endgroup$
– orthocresol
Feb 20, 2016 at 15:11

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