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- Which of the statement is INCORRECT? a. The increase in stability of 2,4-hexadiene over 1,3-hexadiene is due to the increased double bond substitution of the former. b. The stabilization of dienes by conjugation is less pronounced than the aromatic stabilization of benzene. c. Resonance description in alkenes usually involves charge separation. d. Higher energy pi-orbitals often have decreasing number of nodes.Chlordane, like DDT, is an alkyl halide that was used as an insecticide for crops such as corn and citrus and for lawns. In 1983, it was banned for all uses except against termites, and in 1988, it was banned for use against termites as well. Chlordane can be synthesized from two reactants in one step. One of the reactants is hexachlorocyclopentadiene. What is the other reactant?fluorination of alkanes is highly exothermic. Per Hammond’s postulate, assume that the transition state for radical fluorination is almost identical to the starting material. Assuming this fact, estimate the fraction of each monofluoro product formed in the fluorination of 2-methylbutane.
- Give the IUPAC name of the 1,4-addition product of the reaction between 2-methylpenta-1,3-diene with HCl. No need to specify configuration/isomerism. These are reagents that seek a positive center. What is the IUPAC name of the product between the smallest ring that can form a stable cycloalkyne and hydrogen gas in the presence of palladium in calcium carbonate?Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis of chlorocyclohexane?Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation—to a double bond.
- Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl, forms a constitutional isomer, αcyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile— a carbocation—to a double bond.How many total isomers are possible from the mono-chlorination of methylcyclohexane, via radical halogenation?Estimate the stabilization gained as a result of conjugation when 1,4-pentadiene is converted to trans-1,3-pentadiene. Note that the answer is not as simple as comparing the heats of hydrogenation of 1,4-pentadiene and trans-1,3pentadiene. Although the double bonds are moved from unconjugated to conjugated, the degree of substitution of one of the double bonds is also changed, in this case, from a monosubstituted double bond to a trans disubstituted double bond. To answer this question, you must separate the effect that is the result of conjugation from that caused by a change in the degree of substitution.
- A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. How do you account for this difference?1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts. Which of the following correctly describes this new resonance structure? a) It has a double bond between carbons 3 and 4 b) It has a positive charge on carbon 2 c) It has a positive charge on carbon 4 d) It has a double bond between carbons 2 and 3
