Interpretation:
The mechanism of product formation of the given reaction is to be discussed.
Concept introduction:
Electrophiles are electron-deficient species that has positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron-rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Free radical is an atom, molecule, or ion that has unpaired electrons, which makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
The Sommelet-Hauser rearrangement is a rearrangement reaction of benzyl quaternary ammonium salts.
The reagent used in the Sommelet-Hauser rearrangement is the sodium amide or another alkali metal amide.
A tautomer is the constitutional isomer that is readily interconvertible.
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Organic Chemistry
- Which of the following statements is correct? An aldehyde can react with a secondary amine through a nucleophilic addition-elimination mechanism to give an enamine product. A ketone can react with a secondary amine through a nucleophilic addition mechanism to give an imine product. An ketone can react with a primary amine through a nucleophilic addition-elimination mechanism to give an enamine product. An aldehyde can react with a primary amine through a nucleophilic addition mechanism to give an imine product.arrow_forward(D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forwardSeveral additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions.(a) allyl bromide S allylamine (b) ethylbenzene S p@ethylanilinearrow_forward
- Show how you would accomplish the following syntheses using amides as intermediates.You may use any necessary reagents.(a) benzoic acid S benzyldimethylaminearrow_forwardFollowing is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardAldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forward
- Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.arrow_forwardBarbiturates are prepared by treatment of diethyl malonate or a derivative of diethyl malonate with urea in the presence of sodium ethoxide as a catalyst. Following is an equation for the preparation of barbital, a long-duration hypnotic and sedative, from diethyl diethylmalonate an urea. Barbital is prescribed under one of a dozen or more trade names. Propose a mechanism for This reaction The pKa of barbital is 7.4. Which is the most acidic hydrogen in this molecule and how do you account for its acidity?arrow_forwardGive mechanism asaparrow_forward
- Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. p-bromoanilinearrow_forwardShow how you might utilize the reduction of an amide, oxime, or a nitrile to carry out each of the following transformations (a)Benzoic acid to N-ethyl-N-benzylamine (b)1-Bromopentane to hexylamine (c)Propanoic acid to tripropylamine (d)2-Butanone to sec-butylaminearrow_forwardShow how to synthesize the following amines from the indicated starting materials byreductive amination. ) N-cyclohexylaniline from cyclohexanonearrow_forward
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