An unknown alkyl chloride, designated as compound F, forms a Grignard reagent which on treatment with water yields a compound whose formula is C7H16. When compound F is treated with sodium metal 2,2,9,9-tetramethyldecane is formed. What is the structure of compound F? Show your line of reasoning including all equations.
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- 1. The molecular formula of an unknown compound A is C7H14. On ozonolysis, A gave two products B and C where both reacted with 2,4-dinitrophenylhydrazine to give solid derivatives. Compound B gave positive results to both Tollens’ and iodoform tests, while C gave negative results to both of the tests. What is the structural formula of A, B and C. Explain your answer. 2. Compound P, C4H9Br reacts with aqueous solution of sodium hydroxide to form compound Q, C4H10O. Compound Q decolourised acidified solution of potassium permanganate to yield compound R, C4H8O which give an orange precipitate when react with 2,4- dinitrophenylhydrazine. Both compounds Q and R formed yellow precipitate with alkaline iodine solution. Compound P also reacts with magnesium metal to form compound S, C4H9MgBr. Compound R reacts with compound S, followed by hydrolysis to give compound T, C8H18O. Compound T gives off white fumes when react with PCl5. (a) Determine the structural formulae of P, Q, R, S and…Draw structural formulas for (1) the alkyltriphenylphosphonium salt formed by treatment of each haloalkane with triphenylphosphine, (2) the phosphonium ylide formed by treatment of each phosphonium salt with butyllithium, and (3) the alkene formed by treatment of each phosphonium ylide with acetone.X Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►
- Wolff–Kishner reduction (hydrazine, KOH, ethylene glycol, 130°C) of the compound shown gave compound A. Treatment of compound A with m-chloroperoxybenzoic acid (MCPBA) gave compound B, which on reduction with lithium aluminum hydride gave compound C. Oxidation of compound C with chromic acid gave compound D (C9H14O). Identify compounds A through D in this sequence.Structure 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 DAn 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.
- a) Cycohexanone reacts with 1,3-propanediol under acid catalysis to form the cyclic acetal. Write down the reaction mechanism and explain why the use of cyclic acetals as protecting groups is preferred over open- chain acetals. b) Eugenol (see below) is made from cloves. Give the structural formulas of the products which are formed after reaction of eugenol with i) BH3, then H2O2 / NaOH or after reaction with ii) acetic anhydride. OH EugenolCompound EE, C5H10O gives a positive result (formation of silver mirror) when reacted with Tollen’s reagent. Reduction of EE with sodiumborohydride, NaBH4 followed by acidified water, H3O+ produces compound FF. Dehydration of compound FF uses concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound GG. Compound FF also reacts with hot acidified potassium dichromate, K2Cr2O7 to produce 2-methylbutanoic acid, C4H9COOH. Esterification between 2-methylbutanoic acid and methanol, CH3OH produces compound HH. Draw the structural formula of compounds EE, FF, GG, and HH.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.
- Compound A (C11H23Br) is a secondary alkyl halide. On being heated with a solution of sodium ethoxide in ethanol, compound A yielded a mixture of two alkenes B and C, each having molecular formula C11H22. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3,5-diethylheptane. Draw structures for compounds A, B, and C consistent with these observations.7. Compound AA, C4H®O, gives a positive result (formation of a silver mirror) when reacted with Tollen's reagent. Reduction of compound AA with lithium aluminium hydride, LİAIH4 followed by acidified water, H3O* produces an alcohol, BB. Oxidation of BB with hot acidified potassium dichromate, K2Cr207 gives butanoic acid, C3H7COOH. Esterification between butanoic acid and methanol, CH3OH produces compound CC. Dehydration of compound BB using concentrated sulphuric acid, H2SO4 at a temperature of 180°C produces compound DD.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 8r