Interpretation:
The reasonable mechanism for the given reaction is to be proposed.
Concept Introduction:
They can act as nucleophiles and electrophiles in organic reactions.
Amines can be classified into three categories: primary amines, secondary amines, and tertiary amines.
Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which 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 reaction of primary amines with a carbonyl group proceeds via the removal of water, and leads to the formation of an addition product in which nitrogen is doubly bonded to the carbon atom of the carbonyl group.
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Organic Chemistry
- Following 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_forwardThe widely used anticoagulant warfarin (see Chemical Connections: From Moldy Clover to a Blood Thinner in Chapter 18) is synthesized from 4-hydroxycoumarin, benzaldehyde, and acetone as shown in this retrosynthesis. Show how warfarin is synthesized from these reagents.arrow_forwardThe acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. м Br H3C H3C OEt 1. NaOEt 2. H₂O* 3. heat H₂C. Draw curved arrows to show the movement of electrons in this step of the mechanism. CO₂ EtOH CH3 Arrow-pushing Instructions H3C 1:0: :0: :Br: Br: H₂C CH3 CH3 H3C CH3 7barrow_forward
- The acetoacetic ester synthesis is a carbonyl alkylation reaction. It is used to prepare methyl ketones from primary alkyl halides, lengthening the carbon chain by three atoms. Thus, the product can be visualized as being a "substituted acetone." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Br H₂C H3C 1. NaOEt 2. H₂O* 3. heat H₂C. OEt Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H X CO2 CH3 + EtOH :OH На CH3 CO2 CH3 CH3 CH3arrow_forwardThe mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.arrow_forward+ ELOČOET H2N EtO + ELOH Reactions of a primary or secondary amine with diethyl carbonate under controlled conditions gives a carbamic ester. Write a detailed mechanism for this reaction (shown above) which proceeds in 4 steps, including proton transfer steps. Then draw Intermediate 3 in the window provided. The mechanism is detailed as follows: Step 1: Nucleophilic attack to yield zwitterion intermediate 1. Step 2: Protonation/deprotonation (i.e. "proton transfer") of zwitterion 1 to yield intermediate 2. Step 3: Intramolecular collapse of tetrahedral center in intermediate 2 to yield charged intermediate 3. Step 4: Deprotonation of intermediate 3 to yield neutral product. You do not have to consider stereochemistry. In cases where there is more than one answer, just give one. • Do not include counter-ions, e.g., Na",I', in your answer. Do not draw organic or inorganic by-products. Parrow_forward
- From benzene, organic compounds with 6 carbons of less and any other inorganic compund you want. Synthesize the following naphthalene derivative.arrow_forward(3) Propose how to obtain following amine from given starting material. More than one step may be required. Provide all reagents needed for each step and product after each step. gor ~ fromarrow_forward2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis.Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)arrow_forward
- 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_forwardSuggest reagents and draw the mechanism for this reaction.arrow_forwardShow how to convert carboxylic acids to other functional groups, and devisemultistep syntheses using carboxylic acids as starting materials and intermediates.Explain how acid chlorides are used as activated derivatives of carboxylic acidsarrow_forward
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