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- An optically active monoterpene (compound A) with molecular formula C10H18O undergoes catalytic hydrogenation to form an optically inactive compound with molecular formula C10H20O (compound B). When compound B is heated with acid, followed by reaction with O3 and then with dimethyl sulfide, one of the products obtained is 4-methylcyclohexanone. Give possible structures for compounds A and B.Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.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.
- As an example of a ver rare occurence, the following hydrocarbon reacts with two equivalents of butylithium to form a dianion of the formula [C8H6]2- . Propose a structure for this dianion and explain why this dianion forms so readily.Compound A (C9H12) absorbs three equivalents of H2 on a Catalina reduction over a palladium catalyst to give propylcyclohexane. On ozonolysis, compound A give the two products shown below. On treatment with NH2 , NH3 followed by addition of 1_bromo4methylpentane, compound A gave a new hydrocarbon,B (c5H24 ). What are the structures of compound A and B?Compound A has the formula C₂H₁9Cl. B is a C₂H19Br compound. A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products. C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane. Addition of HCI to C yields A as the major product. Propose structures for A and B. • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● ▾ *%-85 ChemDoodle Qt Jn [F 116
- Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*Compound A has the formula C9H19Cl. B is a C9H19Br compound.A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.Addition of HCl to C yields A as the major product.Propose structures for A and B.Draw the organic product obtained on treatment of each of the following two alkenes with bromine: (a) trans-2-pentene and (b) 1- methylcyclohexene. Having done this, draw the product of the reaction of these same alkenes with bromine in aqueous solution.
- Cyclopentene reacts with reacts with ozone in dichloromethane at -78° C. Treatment of the resulting ozonide with zinc in acetic acid or with dimethylsulfide gives A(C3H3O2). Treatment of A with sodium borohydride in ethanol gives B(C3H12O2). Draw the structure of B.In the following sequence of reactions which products are identified correctly? Compound A (C 7H 11B1) is treated with magnesium in ether to give B (C 7H 11MgBr), which reacts violently with D 20 to give 1-methylcyclohexene B with acetone (CH 3COCH 3) followed by hydrolysis gives D (C 10H 180). Heating D with with a deuterium atom on the methyl group C. Reaction concentrated H 2SO 4 gives E (C 10H 16), which decolorizes two equivalents of Br 2 to give F (C 10H 16Br 2). E undergoes hydrogenation with excess H 2 and a Pt catalyst to give isobutylcyclohexane. O The correct structure of C is OH O The correct structure of D is O The correct structure of C is Br OI The correct structure of F is 8rThe treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.