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CN CN NH3 CH;OH Br Br OCH3 not formed

CN CN NH3 CH;OH Br Br OCH3 not formed

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While CH3OH is the solvent in the reaction, and a nucleophilic one, why doesn’t CH3OH act as the nucleophile in this reaction?

The image depicts a chemical reaction and details its failure to produce an expected product. **Chemical Reaction:** 1. **Reactant:** - A compound with a structure consisting of two aromatic rings linked by a double-bonded carbon, with a ketone group (C=O) adjacent to the bromine (Br) on one ring and a cyano group (CN) adjacent to fluorine (F) on the other ring. 2. **Reaction Conditions:** - Reagents: Ammonia (NH₃) and methanol (CH₃OH). 3. **Expected Product:** - The diagram suggests that an attempt was made to replace the fluorine atom with a methoxy group (OCH₃) next to the cyano group. - The product is labeled as "not formed," indicating the reaction did not proceed as planned to yield this particular derivative. The image illustrates the structures of the molecules and indicates the intended but unsuccessful substitution reaction.
Transcribed Image Text:The image depicts a chemical reaction and details its failure to produce an expected product. **Chemical Reaction:** 1. **Reactant:** - A compound with a structure consisting of two aromatic rings linked by a double-bonded carbon, with a ketone group (C=O) adjacent to the bromine (Br) on one ring and a cyano group (CN) adjacent to fluorine (F) on the other ring. 2. **Reaction Conditions:** - Reagents: Ammonia (NH₃) and methanol (CH₃OH). 3. **Expected Product:** - The diagram suggests that an attempt was made to replace the fluorine atom with a methoxy group (OCH₃) next to the cyano group. - The product is labeled as "not formed," indicating the reaction did not proceed as planned to yield this particular derivative. The image illustrates the structures of the molecules and indicates the intended but unsuccessful substitution reaction.
Expert Solution
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A nucleophile is an electron rich species, which can donate electron density in the form of lone pair or π-bond to the center that is electron deficient. For comparison, between two nucleophilic species, one has to consider electron donation ability factor.

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