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The molecule shown by the OP is cis (Z) cinnamic aldehyde - not the ordinary trans (E) cinnamaldehyde. Trans cinnamaldehyde melts at -7.5C, so is liquid at room temperature, and while the melting point of the cis wasn't available, it has been described as a yellowish liquid. The trans isomer is available from fine chemical suppliers at about 50 USD/kg, but ...

4

The reaction wouldn't happen because you forget that $\ce{Cl2}$ is also present in the solution (because $\ce{AlCl3}$ is a strong lewis acid). An acid-base reaction is way faster than an aromatic electrophilic substitution. Once the acid base has happened I doubt that $\ce{AlCl4-}$ would still behave as an electrophile. Footnote: $\ce{AlCl3}$ is a strong ...

3

Converting the comments into an answer; Yes, DMS can be used in place of $\ce{Zn/H2O}$ during the reductive workup for ozonolysis. The mechanism involves DMS reducing a $\ce{O-O}$ fragment of the trioxolane intermediate produced from ozonolysis by one oxygen and itself oxidizing to DMSO (dimethyl sulfoxide). (Image source) I did some literature survey and ...

1

The OP asks why doesn't AlCl$_3$ react with benzene - without Cl$_2$! So, what does aluminum chloride do in benzene? It is slightly soluble in benzene, forming an oily compound (Ref 1, 2). So if you mix AlCl$_3$ with benzene, the "reaction" just goes to a complex and awaits further reactant. Perhaps the Cl atom on an alkyl chloride or on a Cl$_2$ ...

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