A tautomerization reaction can occur with an imine in a way analogous to that of a ketone or aldehyde. Using the appropriate bond energies from Section 1.4, estimate AHan for this reaction and determine which form is more stable, the imine or enamine. NH NH2 Imine Enamine
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- Alcohols react with sulfonyl chlorides to form sulfonate esters. Only the O-H bond of the alcohol is broken in the reaction, and so no inversion of configuration occurs. The resulting sulfonate esters are reactive in SN1 and SN2 reactions since the sulfonate group is a very weak base and is therefore a good leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrange the structure on the image with regard to the reactivity towards nucleophilic acyl substitution 1 being the least and 3 being the mostEnolates are formed by deprotonation of an α-carbon hydrogen. Answer the following questions about enolate formation. In the molecule shown, select the α-carbon hydrogen that would be removed to form an enolate when NaOEt is used as a base. Draw the thermodynamic enolate that results for the molecule in Part 1. Draw only the enolate resonance form that includes a formal charge on the α carbon. Be sure to indicate that formal charge as well as any lone pair of electrons in your answer.
- 1) How will you describe whether any compound has been oxidized or reduced? Support the answer with suitable examples. 2)Why carboxylic acid with a carbonyl group at 3rd position can be decarboxylated? 3) Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position? 4) List the following esters in order of decreasing reactivities towards hydrolysis with reason: Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate 5)LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?Provide a step-wise synthesis for the following: image 1 The last step of the synthesis needs to be a nucleophilic aromatic substitution reaction with a secondary amine.Rearrangements can occur during the dehydration of 1° alcohols even though no 1° carbocation is formed—that is, a 1,2-shift occurs as the C— OH2+ bond is broken, forming a more stable 2° or 3° carbocation, as shown in Equation [1]. Using this information, draw a stepwise mechanism for the reaction shown in Equation [2]. We will see another example of this type of rearrangement in Section 16.5C.
- Which or which of the statements given below is correct. I) Maleic anhydride is a carboxylic acid derivative and its reaction with water is a reduction reaction. II) Fumaric acid and maleic acid are stereoisomers of each other III) Since fumaric acid has a more stable structure than maleic acid, its boiling point is higher. A. Solo I B. I and III C. II and III D. I, II, III E. Solo IIISecondary alcohols are often dehydrated in an E2 reaction to give an alkene. Elimination follows Zaitsev's rule to give the more substituted alkene as the major product. Since the reaction occurs via an E2 mechanism, there is no risk of rearrangement of the carbon skeleton as could possibly occur if the elimination occurred via an E1 mechanism with a carbocation intermediate.Draw curved arrows to show the movement of electrons in this step of the mechanism.The two Grignard reactions and the reduction reaction below are all believed to have similar mechanisms. Use the curved arrow formalism to draw a single mechanism for these reactions using :Nuc-1 to indicate the nucleophile. The reacations are: cyclohexylmagnesium chloride + acetone in ether --> 2-cyclohexyl-2-propanol phenylmagnesium bromide + acetone in ether --> 2-phenyl-2-propanol Acetone + NaBH4 --> 2-propanol
- When allyl bromide is refluxed with magnesium metal in ether solvent, the product formed is 1,5-hexadiene. (C6H10). What is the curved arrow mechanism for this reaction?If the alkenes below were possible products of a elimination reaction ,how would you rank their likely order of formation from most likely to least likely?Complete the curved arrow mechanism of the following double elimination reaction when 2,2-dichloro-3,3-dimethylbutane is treated with two equivalents of sodium amide and heated in mineral oil. A.) Use three curved arrows to show the elimination of the first hydrogen chloride. B.) Use three curved arrows to show the elimination of the second hydrogen chloride. C.) Complete the structure of the organic product formed from the double elimination. The ammonia and chloride ion formed in step 1 is not drawn for clarity.
