what would the chemical reaction, with indicated necessary reagents and conditio
ID: 728412 • Letter: W
Question
what would the chemical reaction, with indicated necessary reagents and conditions, plus the major organic product(s) be for 3,3 - dimethyl- 1- butene with heating with dilute h2so4 (aq)Explanation / Answer
The most common chemical transformation of a carbon-carbon double bond is the addition reaction. A large number of reagents, both inorganic and organic, have been found to add to this functional group, and in this section we shall review many of these reactions. A majority of these reactions are exothermic, due to the fact that the C-C pi-bond is relatively weak (ca. 63 kcal/mole) relative to the sigma-bonds formed to the atoms or groups of the reagent. Remember, the bond energies of a molecule are the energies required to break (homolytically) all the covalent bonds in the molecule. Consequently, if the bond energies of the product molecules are greater than the bond energies of the reactants, the reaction will be exothermic. The following calculations for the addition of H-Br are typical. Note that by convention exothermic reactions have a negative heat of reaction. 1. Addition of Strong Brønsted Acids As illustrated by the preceding general equation, strong Brønsted acids such as HCl, HBr, HI & H2SO4, rapidly add to the C=C functional group of alkenes to give products in which new covalent bonds are formed to hydrogen and to the conjugate base of the acid. Using the above equation as a guide, write the addition products expected on reacting each of these reagents with cyclohexene. Weak Brønsted acids such as water (pKa = 15.7) and acetic acid (pKa = 4.75) do not normally add to alkenes. However, the addition of a strong acid serves to catalyze the addition of water, and in this way alcohols may be prepared from alkenes. For example, if sulfuric acid is dissolved in water it is completely ionized to the hydronium ion, H3O(+), and this strongly acidic (pKa = -1.74) species effects hydration of ethene and other alkenes. CH2=CH2 + H3O(+) ——> HCH2–CH2OH + H(+) The importance of choosing an appropriate solvent for these addition reactions should now be clear. If the addition of HCl, HBr or HI is desired, water and alcohols should not be used. These strong acids will ionize in such solvents to give ROH2(+) and the nucleophilic oxygen of the solvent will compete with the halide anions in the final step, giving alcohol and ether products. By using inert solvents such as hexane, benzene and methylene chloride, these competing solvent additions are avoided. Because these additions proceed by way of polar or ionic intermediates, the rate of reaction is greater in polar solvents, such as nitromethane and acetonitrile, than in non-polar solvents, such as cyclohexane and carbon tetrachloride.
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