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Treatment of a hydrocarbon A (molecular formula
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Organic Chemistry
- A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.arrow_forwardOne compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?arrow_forwardStructure of product C A hydrocarbon, A, with formula C11H16 undergoes hydrogenation with Pd to give product B, C11H22, and with Lindlar's catalyst to give product C, C11 H18. Ozonolysis leads to a mixture of products including cyclohexanone and 4-oxobutanoic acid. Treatment with sodium amide (NaNH2) followed by bromoethane gives compound D, C13H20. Draw possible structures for A, B, C, and D. H₂, Lindlar's Problem 13 of 14 Structure of A 1. NaNH2 Submit 2. CH3CH₂Br Structure of product Darrow_forward
- An achiral hydrocarbon A of molecular formula C7H12 reacts with two equivalents of H2 in the presence of Pd-C to form CH3CH2CH2CH2CH(CH3)2. One oxidative cleavage product formed by the treatment of A with O3 is CH3COOH. Reaction of A with H2 and Lindlar catalyst forms B, and reaction of A with Na, NH3 forms C. Identify compounds A, B, and C. Be sure to answer all parts.arrow_forwardDraw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forwardEast Indian sandalwood oil contains a hydrocarbon given the name santene (C9H14). Ozonolysis of santene gives the compound shown. What is the structure of santene?arrow_forward
- Hydrocarbon A has the formula C9H12 and absorbs 3 equivalents of H2 to yield B, C9H18, when hydrogenated over a Pd/C catalyst. On treatment of A with aqueous H₂SO4 in the presence of mercury(II), two isomeric ketones, C and D, are produced. Oxidation of A with O3 gives a mixture of acetaldehyde (CH3COH) and the trialdehyde shown below. Propose structures for compounds A-D. CH,CHO OCHCH,CHCH CHOarrow_forwardA certain compound of molecular formula C19H38 was isolated from fish oil and from plankton. On hydrogenation it gave 2,6,10,14-tetramethylpentadecane. Ozonolysis gave (CH3)2C O and a 16-carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?arrow_forwardHydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forward
- Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?arrow_forwardIn 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 8rarrow_forwardAlcohol A (C10H18O) is converted to a mixture of alkenes B and C on being heated with potassium hydrogen sulfate (KHSO4). Catalytic hydrogenation of B and C yields the same product. Assuming that dehydration of alcohol A proceeds without rearrangement, deduce the structures of alcohol A and alkene C.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning