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- The reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism. Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result.An unknown hydrocarbon G, whose formula is C16H26 contains two triple bonds. Ozonolysis followed by reduction with (CH3)2S gave CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. Suggest a reasonable structure for compound G.The hydroboration–oxidation of internal alkynes produces ketones.(a) When hydroboration–oxidation is applied to but-2-yne, a single pure product isobtained. Determine the structure of this product, and show the intermediates in itsformation.
- Please help with the following ochem question... start with cyclohexene and employing a Dieckmann cyclization, show how the compound in the image below can be prepared. Provide the bond line structures of the major organic product obtained in each step of the proposed synthesis. **I think the compound that is formed in the image is methyl-2-oxycyclopentane-1-carboxylate**A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactionsIn the presence of acid such as H2SO4, 3,4-dimethyl-1-pentene undergoes isomerization to 2,3-dimethyl-2-pentene (shown below). Write a complete mechanism, showing all steps and using curved arrows to explain this observation.
- A hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.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.
- Help with the following ochem reaction scheme... Consider 3,4-dimethylpiperidine being subjected to the below reaction scheme: step 1) CH3I (excess) step 2) NaOH, heat step 3) CH3I (excess) step 4) NaOH, heat Provide the bond line structures for the major organic product obtained in each step and then discuss the regiochemistry for step 2.Suggest a strategy for converting 1-methylcyclohexene into 1-cyclohexylmethanol. Provide the structures for the major organic products frormed in each step.An unknown hydrocarbon decolorizes bromine in CCl4CCl4, and it undergoes catalytic reduction to give cis-decalin. When treated with warm, concentrated potassium permanganate, this compound gives cis-1,2-cyclohexanedicarboxylic acid. Propose a structure for the unknown compound.