This functional group can be added to arenes (“AIR-eens”) using the Vilsmeier–Haack reagent, which is formed in situ from phosphorus oxychloride and DMF. For 10 points each:
[10h] Name this functional group added to phenols using chloroform and a strong base in the Reimer–Tiemann reaction. An industrial process for adding this functional group to alkenes uses rhodium complexed to sodium salts of sulfonated triphenylphosphine.
ANSWER: formyl group [accept formylation or hydroformylation; accept aldehyde; accept CHO or COH; prompt on carbonyl or CO] (The industrial process is the Ruhrchemie/Rhone–Poulenc process, and the ligand is TPPTS.)
[10m] Deprotonating chloroform generates these compounds for EAS (“E-A-S”) in the Reimer–Tiemann reaction. Lone pairs of the N-heterocyclic type of these compounds coordinate ruthenium in Grubbs catalysts used for olefin metathesis.
ANSWER: carbenes [accept N-heterocyclic carbenes or NHCs; accept persistent carbenes; accept dichlorocarbenes]
[10e] The Reimer–Tiemann reaction has largely supplanted Gattermann–Koch formylation for the production of salicylaldehyde (“SAL-uh-sill-aldehyde”) due to the latter’s use of this toxic gas that competes with O2 for binding to hemoglobin.
ANSWER: carbon monoxide [or CO]
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