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- Although the Diels–Alder reaction generally occurs between an electronrich diene and an electron-deficient dienophile, it is also possible to have inverse-demand Diels–Alder reactions between suitable electrondeficient conjugated double bonds and electron-rich alkenes. These reactions are particularly useful because they allow for the incorporation of heteroatoms into the new six-membered ring. Predict the products of each inverse-demand Diels–Alder reaction below. Be sure your products reflect the correct stereochemistry. If more than one regioisomer is possible, draw both.74. When piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substituted piperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and 3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene? 1. еxcess CHз!/К2CO3 2. Ag20, H20 3. Д 1. еxcess CHз!/K2CO3 2. Ag20, H20 CH3NCH,CH,CH;CH=CH2 3. A CH2=CHCH2CH=CH2 || `N' H CH3 1,4-pentadiene piperidineDraw the structures of the diene and dienophile that would be used in the diels alder reaction to synthesize the following compounds. Label each structure as diene or dienophile.
- Determine all of the products obtained from the addition of HCl to the 1,3-diene. Once determined, draw a mechanism that accounts for the formation of every product. Then, Identify and account for the formation of the major adduct/or adducts under these conditions assuming that the reaction is conducted under thermodynamic conditions.Treatment of the diene shown with excess ozone followed by a reductive work-up produces.Electrophilic addition to an alkene proceeds via Markovnikov regiochemistry due to the formation of the more stable carbocation intermediate. In the case of conjugated dienes, that is dienes that are separated by one sigma bond, the carbocation that is formed is stabilized additionally by resonance. Addition of the nucleophile to the carbocation intermediate can therefore give two types of products: direct addition to the double bond, also called 1,2-addition, and conjugate addition to the resonance stabilized carbocation, also called 1,4-addition.Allylic carbocation stability is affected by both the nature of the carbocation (primary allylic, secondary allylic, or tertiary allylic) and by the degree of substitution of the double bond. The latter is typically the dominant effect and so a primary allylic carbocation with a trisubstituted double bond is more stable than a tertiary allylic carbocation with a monosubstituted double bond.Electrophilic addition to a conjugated diene is…
- piperidine undergoes the series of reactions shown here, 1,4-pentadiene is obtained as the product. When the four different methyl-substitutedpiperidines undergo the same series of reactions, each forms a different diene: 1,5-hexadiene; 1,4-pentadiene; 2-methyl-1,4-pentadiene; and3-methyl-1,4-pentadiene. Which methyl-substituted piperidine forms which diene?Please provide the name of the dienes and dienophiles, and their products and explain the reaction that took place in each item.In the reaction below, 3-Buten-2-one reacts with 2,3-Dimethyl-1,3-butadieneand 1,3-Butadieneat 140°C and 30°C, respectively. Explain why these two dienes react at different temperatures.
- 5. When the diene below is dissolved in THF solvent to which a small amount of H₂SO4 has been added, cyclic products are formed that are isomeric with the reactant. Write a mechanism for the formation of ONE of these cyclic isomers, and include its structure. (In other words, you predict the product structure by going through the mechanism.) Include curved arrows in the mechanism to show bonding changes. yand H₂SO4 THF A cyclic isomer of the reactantAlkyl 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…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…