Determine which nucleophilic aromatic substitutions are likely, and proposemechanisms for both the addition–elimination type and the benzyne type.
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Q: State the effects of substituents on a benzene derivative towards further aromatic substitution.
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A: Aromatic Electrophilic substitution reactions:
Determine which nucleophilic
mechanisms for both the addition–elimination type and the benzyne type.
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- In nucleophilic aromatic substitution reactions that proceed by the nucleophilic addition-elimination mechanism, the reaction rate increases as the electronegativity of the halogen leaving group increases: Ar-I < Ar-Br < Ar-CI < Ar-F. Which step does this suggest is the rate-determining step of the mechanism-the addition step or the elimination step? Explain.What are the steps of the mechanism of reaction . Electrophilic aromatic substitution. Is it Ortho,para,meta ?Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*
- Aromatic heterocyclic chemistry: State whether the following drugs are aromatic heterocycles and if they follow the 4 aromaticity rules (unsaturation, (4n + 2)pi electrons, cyclic and flat/planar), NAME ANY HETEROCYCLES. Draw the structure of the core of any aromatic heterocycles in the drug. Riociguat, Imatinib, Clopidogrel, Glatiramer acetate, AxitinibThe Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?b) Fill in the gaps by drawing the structures of the missing reagents, intermediates and/or products of the following electrophilic aromatic substitutions. Chemical formulas have been added for guidance. . Step 1 Step 2 CH3 HNO. 1. CH;NO2 C;H3N Pd/C NO2 3 1 2 4 CH3 Brz FeBr C3H;Bro 6 Using resonance structures, justify whether the acetyl group of compound 5 will direct the bromination reaction to the meta or ortho/para positions
- b) Fill in the gaps by drawing the structures of the missing reagents, intermediates and/or products of the following electrophilic aromatic substitutions. Chemical formulas have been added for guidance. Step 1 Step 2 CH3 HNO3 H2 1. C6H5NO2 C,HgN H2SO4 `NO2 Pd/C 1 2 4 CH3 Br2/FeBr3 C3H;Bro 5 6 Using resonance structures, justify whether the acetyl group of compound 5 will direct the bromination reaction to the meta or ortho/para positions.Aromatic heterocyclic chemistry: State whether the following drugs are aromatic heterocycles and if they follow the 4 aromaticity rules (unsaturation, (4n + 2)pi electrons, cyclic and flat/planar), NAME ANY HETEROCYCLES Vildagliptin, Valbenazine, Levetiracetam, (Dolutegravir/Lamivudine)CH3 Br,/FeBr3 C3H;BrO 5 Using resonance structures, justify whether the acetyl group of compound 5 will direct the bromination reaction to the meta or ortho/para positions.
- In SN2 reactions of haloalkanes, the order of reactivity is RI>RBr>RCl>RF. Alkyl iodides are considerably more reactive than alkyl fluorides, often by factors as great as 106. All 1-halo-2,4-dinitrobenzenes, however, react at approximately the same rate in nucleophilic aromatic substitutions. Account for this difference in relative reactivities.Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…Which of the following assertions most accurately defines alkynes' overall reactivity? Alkynes undergo electrophilic addition reactions just like alkenes. An alkyne reacts as an electrophile and is therefore electron rich. An alkyne reacts as a nucleophile and is therefore electron poor. An alkyne reacts as an electrophile and is therefore electron poor.