# Number of stereoisomers of 3-ethyl-1-pentene-1,4-diol

I am trying to figure out how many stereoisomers this compound has. I know that there are two chiral carbon atoms, which allow $2\times2 = 4$ possible isomers. There is also a double bond which, as far as I know, doubles the number of stereoisomers, since there are now four possibilities for the cis-isomer, and four for the trans-isomer. So I thought the total number of stereoisomers was eight, but my teacher told me the answer was six. I have thought about it for a while, but I can't figure out why it should be six. What did I do wrong?

• Ask your instructor for the six stereoisomers. The answer is 8 to me. – jerepierre May 22 '16 at 13:46
• question is misleading. Only 4 are possible. We should also take into account of tautomerization. – adianadiadi May 22 '16 at 18:57