Interpretation:
The structures of the compounds A and B are to be identified on the basis of the information given and the symbol for the reaction mechanism by which A is converted to B under the given reaction conditions is to be identified.
Concept Introduction:
>Ozonolysis of
If formaldehyde is produced after ozonolysis, the alkene has a terminal double bond.
>If an aldehyde is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene has a hydrogen attached to it.
>If a ketone is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene must be disubstituted.
Want to see the full answer?
Check out a sample textbook solutionChapter 8 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
- Compound X has the molecular formula C7H14. Hydrogenation of compound X produces 2,4-dimethylpentane. Hydroboration-oxidation of compound X produces a racemic mixture of 2,4-dimethyl-1-pentanol. Predict the major product(s) obtained when compound X is treated with aqueous acid (H3O*). Draw all the substrates, reagents, and productsarrow_forwardAn unknown hydrocarbon A with the formula C6H10 reacts with 1 molar equivalent of H2 over a palladium catalyst to give B C6H12 (Rxn 1). Hydrocarbon A also reacts with OsO4 to give the glycol C (Rxn 2). A gives 5-oxohexanal on ozonolysis (Rxn 3). Draw the structures of A, B, and C. Give the reactions.arrow_forwardAn alkene is treated with OsO4 followed by H2O2. When the resulting diol is treated with HIO4, the only product obtained is an unsubstituted cyclic ketone with molecular formula C6H10O. What is the structure of the alkene?arrow_forward
- A 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_forwardA 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_forwardWhen 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).arrow_forward
- Compound A has molecular formula C7H15B.. Treatment of compound A with sodium ethoxide yields only one elimination product (compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which has molecular formula C7H160. Draw the structures of compounds A, B, and C.arrow_forwardCompound A(C7H15Br) is not a primary alkyl bromide. It yields a single alkene(compound B) on being heated with sodium ethoxide in ethanol. Hydrogenation of compound B yields 2,4-dimethylpentane. Identify compounds A and B.arrow_forward7. You discover a bottle of compound A with the label "C8H₁4" in the lab. Compound A decolourizes Br2 in CCl4 and becomes compound B (C8H14Br2). Treatment of B with two moles of potassium hydroxide produces compound C. Treatment of C with acidic potassium permanganate produces two four- carbon compounds: a diketone and a dialdehyde, respectively. However, treatment of A with acidic potassium permanganate produces only one product-compound D (shown below). Identify compounds A through C, clearly showing how you reached your conclusions. e Darrow_forward
- 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 8rarrow_forwardCr(VI) compounds are common reagents for the oxidation of alcohols. Primary alcohols are oxidized to carboxylic acids and secondary alcohols are oxidized to ketones. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced Cr(IV) compound as the leaving group.Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forwardDraw the structure of (2Z, 6E)-3-ethyl-7-methyldeca-2, 6-dien-1-ol, the sex pheromone of the codling moth, a common agricultural pest that destroys apple crops. By spraying an apple orchard with this pheromone, the mating of male and female moths is disrupted, and moth populations can be controlled.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning