Concept explainers
(a)
Interpretation: The structures including stereochemistry of the methyl esters of endiandric acids D and E is to be drawn.
Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the
(b)
Interpretation: The methyl ester of endiandric acid E undergoes an intramolecular
Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.
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Chapter 27 Solutions
ORGANIC CHEM W/CNCT+SOLUTION MANUAL >BI<
- An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions, and show your reasoning.arrow_forwardUnsymmetrical alkene (1-butene) may be converted to Glycol by which of the following reactions options: Hydroboration in presence of hydrogen peroxide and NaOH Hydration in presence of acidic aqueous medium Oxidation with permangante Oxidation with Oxygen in presence of silver catalyst at 250 C and high pressure Ozonolysis in presence of Zinc and acidic mediumarrow_forwardAn organic compound A which has a characteristic odour is treated with 50% NaOH to give B (C7H8O)and C which is a sodium salt of an organic acid . Oxidation of B gives back A. Heating C with soda lime yields an aromatic hydrocarbon D . Deduce the structures of A,B,C and Darrow_forward
- Compound A, C9H16 reacts with 1 molar equivalent(s) of hydrogen on catalytic hydrogenation. A undergoes reaction with ozone, followed by Zn treatment. What is the structure for A?arrow_forwardCompound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…arrow_forwardThe bicyclic alkene P can be prepared by thermal electrocyclic ring closure from cyclodecadiene Q or by photochemical electrocyclic ring closure from cyclodecadiene R. Draw the structures of Q and R, and indicate the stereochemistry of the process by which each reaction occurs.arrow_forward
- Compound A has molecular formula C4H10, and gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D, where C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G, respectively, both of which are of molecular formula C4H10O. What are the names of compounds A-G?arrow_forwardStearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?arrow_forwardAn organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.arrow_forward
- Treatment of propylbenzene with NBS + hv affords a single constitutional isomer. Suggest a structure for the product and a reason for its formation.arrow_forwardHydrocarbon 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 KMnO4 gives a mixture of acetic acid (CH3COOH) and the tricarboxylic acid E. Propose structures for compounds A-D, and write the reactions.arrow_forwardα-Terpinene, C10H16, is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst, α-terpinene reacts with 2 molar equivalents of H2 to yield a hydrocarbon, C10H20. On ozonolysis, followed by reduction with zinc and acetic acid, α-terpinene yields two products, glyoxal and 6-methyl-2,5- heptanedione. (a) How many degrees of unsaturation does a-terpinene have? (b) How many double bonds and how many rings does it have? (c) Propose a structure for a-terpinene.arrow_forward