CO2H A CH;CO,H HO,C .CO,H acetic acid E Oxidation products

Compound A, CH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CH4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, jtust draw one.

Please draw out the structures of compound A, B and C. Compound A, B and C have the same molecular formula C4H6. All of the compounds can make bromine decolored. Compound A reacts with AgNO3 in ammonia solution to form white solid. Compound B undergoes cycloaddition reaction with maleic anhydride at room temperature. Compound C is oxidized with KMN04 to only give one quivalent of carboxylic acid. Please write out the structures of compound A, B and C.

Compound A has the formula C10H16. When treated with hydrogen and palladium, Compound A takes up 1 equivalent of H2, forming Compound B. When Compound A is treated with ozone followed by zinc, Compound C forms with the formula C10H16O2. Compund C is a symmetric diketone. Provide structures for Compound A and the reaction products. Select to Draw Compound B H2, Pd/C

meta-Chloroperoxybenzoic acid (m-CPBA) is not the only peroxy acid capable of reacting with alkenes to form epoxides. For the reaction below: H3C H3C + CH3CO3H a Draw the structure of the major organic product derived from the alkene.

An optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with EtMgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6 (A tricarboxylic acids is a compound with three - CO2H groups.). Give the structure of A, and account for all observations.

Suggest a strategy for converting 1-methylcyclohexene into 1-cyclohexylmethanol. Provide the structures for the major organic products frormed in each step.

The academic version of the process invention program (PIP) contains several examples, as follows: HDAl-hydrodealkylation of toluene to produce benzene CYHEXl-cyclohexane production by hydrogenation of benzene STYRl-styrene production from ethylbenzene XYLl-production of m-xylene from toluene ANHYDl-reaction of acetone and acetic acid to form acetic anhydride BUTALl-alkylation reaction of butene-1 and isobutane to produce iso-octane Select the “new plant design” mode and the “look at existing flow sheet” option, and follow the synthesis steps for one of these processes. ‘Obtain the current flow sheet as output at each level of the synthesis procedure. Also list the heuristics used at each step.