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Provide the major organic product for each of the following transformations

Chemistry Dec 29, 2020

Provide the major organic product for each of the following transformations. 

tcA11-14 HCN 
0-Th H2 trace H 

2) H• 
H 0 

H• 
\••?  9/trace Fi• (c6H0,p--a-12-' 
 

Expert Solution

1.Explanation | Hint for next step

The nucleophilic carbon of cyanide ion adds to electrophilic carbon of carbonyl carbon results in the breaking of carbon-oxygen double bond. The oxide formed in this step abstracts the proton to form a cyanohydrin product.

2.Explanation | Common mistakes | Hint for next step

The carbonyl compounds are protected as acetals in acidic medium. Cyclic acetals are the compounds having two ether oxygen atoms attached to the same carbon. The reaction of ethylene glycol with cyclohexanone forms cyclicacetals.

3.Explanation | Common mistakes | Hint for next step

The following is Wittig reaction in which the conversion of \left( {{\rm{C = O}}} \right){\rm{to }}\left( {{\rm{C = C}}} \right)(C=O)to(C=C) bond takes place. The nucleophilic carbon atom of ylide reacts with a electrophilic carbon of the cyclohexanone and electrons and migrates into a positive charged phosphorus atom by four membered cyclic intermediate (oxophosphetane).

4.Explanation | Common mistakes | Hint for next step

Cyclohexanone on reaction with pyrrolidine (secondary amine) undergoes a nucleophilic addition reaction to give enamines. Nitrogen atom of pyrrolidine acts as a nucleophile and attacks the carbonyl carbon in acidic medium followed by the process of removal of water which gives the enamines.

5.Explanation | Hint for next step

Cyclohexanone on reaction with aniline (primary amine) undergoes a nucleophilic addition reaction to give imines. Nitrogen atom of aniline acts as a nucleophile, attacks the carbonyl carbon of cyclohexanone in acidic medium and forms carbinolamine (unstable product) followed by the process of removal of water which gives the imines.

6.Explanation

Cyclohexanone on reaction with Lithiumaluminumhydride \left( {{\rm{LiAl}}{{\rm{H}}_4}} \right)(LiAlH4?) undergoes a reduction reaction to give alcohols. The hydride ion from \left( {{\rm{LiAl}}{{\rm{H}}_4}} \right)(LiAlH4?) acts as a nucleophile and attacks the carbonyl carbon of cyclohexanone in acidic medium to form cyclohexanol.

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