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Organic Chemistry - Standalone book
- Fill in the table with the partial charges of the atoms. The atoms are numbered with the following scheme with respect to the substituent on the aromatic ring. x c/ 3. | H./ Atom Chlorobenzene Nitrobenzene Aminobenzene C2 Ca Which substituent results in a ring atom with the greatest positive charge (smallest negative charges)? What is the mechanism that causes this pattern of electron distribution on the aromatic ring? Diagram the mechanism. Which substituent results in a ring atom with the least positive charge (largest negative charges)? What is the mechanism that causes this pattern of electron distribution on the aromatic ring? Diagram the mechanism.arrow_forwardDraw the product of the reaction shown below. Use dash and/or wedge bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts. OH 11110 PC|3 pyridine Qarrow_forward3A. During the workup portion of the reaction of alkenes with HBr as described in the experiment provided, a student transferred the reaction mixture to a separatory funnel, rinsed the reaction flask with diethyl ether, and added the ether rinses to the separatory funnel. The student then added sodium bicarbonate to the separatory funnel. Extremely vigorous bubbling occurred. What did the student do wrong? Can they still isolate the product? If so describe the next steps the student should take to isolate the product.arrow_forward
- Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodomethane with the following alkoxide ion: CH3 H3C O Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. орy вste ChemDoodlearrow_forwardThe 2-propenyl cation appears to be a primary carbocation, and yet it is considerably more stable than a 1° carbocation such as the 1-propyl cation. CH,=CH-CH, CH, CH, CH," 2-Propenyl cation 1-Propyl cation How would you account for the differences in the stability of the two carbocations?arrow_forwardWrite an equation for the acid-base reaction between 2,4-pentanedione and sodium eth- oxide and calculate its equilibrium constant, K. The pK, of 2,4-pentanedione is 9; that of ethanol is 15.9. CH,CCHÖCH, + CH,CH,O Na* H 2,4-Pentanedione Sodium ethoxidearrow_forward
- The reaction shown below is carried out in two stages. In the first, the two reactants are combined in tetrahydrofuran (THF) solvent to form a neutral adduct. Aqueous acid is then added to hydrolyze this initial adduct, giving the final product. N(CH3)2 I. H a For the reaction shown above, draw the major organic product having at least one carbonyl group. • You do not have to consider stereochemistry. Pis 85 1. THF 2. H3O+ n [ ]#arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodoethane with the following alkoxide ion: H3C CH3 + Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. P opy aste [*arrow_forward
- 1. You are planning to carry out a reaction between butyne CH3CH₂C=CH, and sodium methoxide, CH3ONa. You also need to choose an appropriate solvent for the reaction. Would H₂O be an appropriate solvent? Explain your rationale.arrow_forwardChemistry 3. The following sequence generates crystals. The crystals produced are insoluble in organic solvents but freely soluble in water. They have a melting point of 203 °C. There is an instantaneous precipitate formed with silver nitrate solution. Catalytic hydrogenation gives cycloheptane. What is the crystalline compound? Why does it have these unexpected properties? heat 1 equiv Br2 dibromide crystals - HBr tropilidenearrow_forwardA compound X of molecular formula C7H14 when hydrogenated produces 2,4-dimethylpentane and when hydroborated the obtained alcohol is 2,4-dimethyl-1-pentanol. a. What is the structure of X? b. If X is reacted with H2O catalyzed by H2SO4, what product is obtained? Write the structure, give the name, and write the complete mechanism, step by step of this reaction, in such a way as to explain the formation of the compound (DO NOT FORGET THE CORRECT USE OF ARROWS!).arrow_forward
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