#SmilesC

A coffee morning quiz for chemists ...

• #SmilesC this cpd was designed as a weapon, what is it?  OC(c1ccccc1)(c2ccccc2)C(=O)OC1CN(CC2)CCC12

I'm going to post some SMILES structures with related questions on twitter under the hashtag #SmilesC (the C standing for chemistry); I'd be curious if anyone could work-out the answer without using any software; if you can, post the answer in the comments section below. Kudos to the first to post! Acknowledgement is due to K J Haxton who has been doing this sort of thing on her blog Endless Possibilities for quite a while. For those who are unfamilliar with SMILES - Simplified Molecular Input Line Entry Specification - it is a method of describing the structures of molecules in 1D instead of representing them in 2D as is usual. The theory of smiles can be found from the Daylight company. A useful decoding webpage can be found at DEPICT. If you copy the following molecule, CC(=O)C into the form on the DEPICT website, the structure of the molecule (acetone) will be returned. Another useful piece of software - for checking purposes only - is ChemSpider.

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Questions asked to date with links to answers (when the answer is posted in the comments section).

1. #SmilesC what is the name of this vitamin? OC[C@H](O)[C@@H]1C(O)=C(O)C(=O)O1
   
2. #SmilesC name this reaction c1ccccc1C=O>CC(=O)OC(=O)C.[O-]C(=O)C>c1ccccc1C=CC(=O)O
   
3. #SmilesC what is this compound called? If not wonderland, where is it found? C=CC[S+]([O-])SCC=C
   
4. #SmilesC what's special about this arrangement of atoms? [Rb+].[Na+].O=C([O-])[C@H](O)[C@@H](O)C(=O)[O-].O.O.O.O
   
5. #SmilesC what has this compound got to do with the law? O=N(=O)C1=CC=C(O1)C=NN2CCOC2(=O)
   
6. #SmilesC what is so controversial about this compound? [Na+].[S-]C1=NC(=O)C(C(C)CCC)(CC)C(=O)N1
   
7. #SmilesC what is being prepared here? OCCSCCO>HCl.HCl>ClCCSCCCl
   
8. #SmilesC whose degradation is used to prepare this compound? CC(=O)C1CCC2C1(C)CCC3C4(C)CCC(=O)C=C4CCC23
   
9. #SmilesC some say this cpd has save more lives than any other, what is it? ClC(Cl)(Cl)C(c1ccc(Cl)cc1)c2ccc(Cl)cc2
10. #SmilesC this cpd was designed as a weapon, what is it? OC(c1ccccc1)(c2ccccc2)C(=O)OC1CN(CC2)CCC12