A Suppose the molecule below is in acidic aqueous solution. Is keto-enol tautomerization possible? • If a keto-enol tautomerization is possible, draw the mechanism for it. Be sure any extra reagents you add to the left-hand side of the first step are readily available in this solution. • If a keto-enol tautomerization is not possible, check the box under the drawing area. OH 2 Add/Remove step X G Click and drag to start drawing a structure.
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- Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. H3C NH₂ HCI/H₂O reflux • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one.Is the product of this reaction more or less soluble than the initial molecule? Why? 1. RCO;H 2. H*, H,O Less water-soluble More water-soluble Water-solubility improved due to a negative charge on the product. Water-solubility improved due to a positive charge on the product. The product now has sufficient H-bonding functional groups to support water-solubility. An acetal has been formed which would decrease the water-solubility Another reason2) After each reaction arrow, draw the structure of the expected major organic product(s). Ме НО. CS2CO3 Me + DMF O2N "Ме Ме
- 3. Provide the mechanism for the following reversible nucleophilic addition. Show all curved arrows and intermediates. cat. H+ H₂O HO OH H H 1) protonate to activate 2) nucl adds 3) deprotonate what staysb).. .. Under each potential product of this E2 elimination, write "major product," "minor product," or "not formed." Me Br H Me Me OH Me Ph Ph H Me H Et Me Me Me Ph Ph Me Me EtNonconjugated B,y-unsaturated ketones are in base-catalyzed equilibrium with their conjugated a,ß-unsaturated isomers. The mechanism of interconversion involves the formation of a resonance-stabilized intermediate with three resonance contributors. Draw the structures of these three resonance contributors. OH • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate resonance structures using the symbol from the drop-down menu. + *** Sn [F
- Chemistry Please help explain this textbook question: Although N, N -dimethylaniline is extremely reactive toward electrophilic aromatic substitution and is readily substituted by weak electrophiles, such as diazonium and nitronium ions, this reactivity is greatly diminished by the introduction of an alkyl substituent in an ortho position.Show a detailed mechanism for the following reaction. Include all arrows and steps. H₂CH₂ - OH H₂O но OH1. Show all steps in the synthesis of 4-methylaniline from toluene. Clearly show all reagents, reactants and products for each step. Toluene -------> --------> 4-methylaniline
- rank these from least to most reactive in nucleophilic acyl substitution with a nucleophile I)CH3COOC2H5 II) CH3COO-Na+ III)CH3COCl IV) CH3CONH2• Same reagents as acid-catalyzed dehydration, except starting with a instead of an alcohol. • Same as the general mechanism hydrohalogenation, except with . Remember that EVERY acid-cat. mechanism begins with General Reaction: EXAMPLE: Provide H₂O H₂SO4 EXAMPLE: Provide the mechanism for the following addition reaction. H₂O H₂SO4 OH WH H₂O H₂SO4 as the nucleophile and ends with do PRACTICE: Provide the mechanism and predict the product of the following reaction. MAXOWhich of the following would be a better starting material for a nucleophilic aromatic substitution reaction? Explain your choice using structures. Then provide the complete arrow pushing mechanism for the reaction of the better starting material and excess ethanol. CI CI O₂N NO₂ NO₂ NO₂