Which structure is the product of the reaction of 4-tert-butyl-2-octanone and NaCN?

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Quizplus · Accepted Answer

11ecba2d_126b_ec64_a3bf_83f2a5c9321d_MD0008_00 Molecular structure determines how a reaction will proceed. The following steps describe how to determine the structure of an organic molecule from its name: Determine the number of carbon atoms in the parent chain, which is the longest chain containing the highest priority functional group. The prefix of the parent alkane determines the number of carbons, and the suffix describes the high priority functional group. The number prior to the chain name describes the carbon to which the main functional group is attached. Determine the position and identity of each substituent, if any. All substituent names are placed at the beginning of the compound name, together with the number of the carbon to which the substituent is attached. The reactant 4-tert-butyl-2-octanone has an eight-carbon parent chain denoted by the prefix oct-, and the suffix -one indicates the compound is a ketone with the carbonyl at carbon 2. The substituent is a tert-butyl on carbon 4. The reaction of a ketone or an aldehyde with a cyanide ion (from NaCN) acting as a nucleophile and attacking the electrophilic carbonyl (C=O) carbon produces a cyanohydrin. The cyanohydrin functional group contains a hydroxyl group (-OH) and a cyano group (C≡N) attached to the same carbon. (Choice A) This structure shows the correct addition of CN to the carbonyl; however, the compound contains an isobutyl group instead of a tert-butyl on C4. (Choices B and C) These structures show the addition of CN to the carbonyl oxygen instead of the carbonyl carbon. The starting material from Choice B contains an isobutyl group instead of a tert-butyl on C4. Educational objective: The reaction of a ketone or aldehyde with sodium cyanide (NaCN) results in the nucleophilic attack of the carbonyl by the cyanide ion, and produces a cyanohydrin. Organic molecules are named after the number of carbon atoms in the longest carbon chain, adding the suffix of the highest priority functional group. Substituent names precede the chain name, and the location of the high-priority group is denoted by placing its location between the substituent and chain names.

Which Structure Is the Product of the Reaction of 4-Tert-Butyl-2-Octanone