Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 8, Problem 51P
On being heated with a solution of sodium ethoxide in ethanol, compound A
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Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout
On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a mixture of two alkenes B and C, each of which had the molecular formula C7H14. Catalytic hydrogenation of major isomer B or minor isomer C gave only 3-ethylpentane. Suggest structures and mechanisms for compounds A, B, and C consistent with these observations.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
Chapter 8 Solutions
Organic Chemistry - Standalone book
Ch. 8.1 - What three alkenes yield 2-methylbutane on...Ch. 8.2 - Prob. 2PCh. 8.2 - Prob. 3PCh. 8.3 - Prob. 4PCh. 8.4 - Prob. 5PCh. 8.4 - Give a structural formula for the carbocation...Ch. 8.5 - Prob. 7PCh. 8.6 - Instead of the three-step process of Mechanism...Ch. 8.6 - The rates of hydration of the two alkenes shown...Ch. 8.6 - Is the electrophilic addition of hydrogen chloride...
Ch. 8.7 - You can calculate the equilibrium constant for the...Ch. 8.7 - Does the presence or absence of a catalyst such as...Ch. 8.7 - The gas phase reaction of ethanol with hydrogen...Ch. 8.8 - Prob. 14PCh. 8.8 - Hydroborationoxidation of -pinene, like its...Ch. 8.10 - Arrange the compounds 2-methyl-1-butene,...Ch. 8.10 - Give the structure of the product formed when each...Ch. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.12 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.13 - Prob. 22PCh. 8.14 - Prob. 23PCh. 8.14 - Prob. 24PCh. 8 - How many alkenes yield...Ch. 8 - Prob. 26PCh. 8 - Catalytic hydrogenation of...Ch. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - A single epoxide was isolated in 7984% yield in...Ch. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - On catalytic hydrogenation over a rhodium...Ch. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - 1-Butene has a higher heat of hydrogenation than...Ch. 8 - Match the following alkenes with the appropriate...Ch. 8 - The heats of reaction were measured for addition...Ch. 8 - Complete the following table by adding + and -...Ch. 8 - Match the heats of hydrogenation (107 kJ/mol,...Ch. 8 - The iodination of ethylene at 25 C is...Ch. 8 - Specify reagents suitable for converting...Ch. 8 - (a) Which primary alcohol of molecular formula...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Prob. 50PCh. 8 - On being heated with a solution of sodium ethoxide...Ch. 8 - Compound A (C7H15Br) is not a primary alkyl...Ch. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - A mixture of three alkenes (A, B, and C) was...Ch. 8 - Reaction of 3,3-dimethyl-1-butene with hydrogen...Ch. 8 - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol...Ch. 8 - Prob. 58PCh. 8 - East Indian sandalwood oil contains a hydrocarbon...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - On the basis of the mechanism of acid-catalyzed...Ch. 8 - As a method for the preparation of alkenes, a...Ch. 8 - Which of the following is the most reasonable...Ch. 8 - Prob. 68PCh. 8 - Oxymercuration Concerns about mercurys toxicity...Ch. 8 - Prob. 70DSPCh. 8 - Prob. 71DSPCh. 8 - Prob. 72DSPCh. 8 - Prob. 73DSPCh. 8 - Oxymercuration Concerns about mercurys toxicity...
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- Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (Ch3COCH3) followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.arrow_forwardCompound A has molecular formula C4H10. Compound A 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, whereas 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 C4H100. What are the chemical names of compounds A-G?arrow_forward> acetone > ethane - Two molecular ions H3C-CH₂-CH₂-COR and have undergone McLafferty rearrangement and Ortho effect respectively. What are the possible fragments obtained as a result of these processes ? COOCH3 OH + -COH]: [CH₂O and Co] CO (A) (B) x] : [GH₂C (C) RH, C₂H₂ and CH₂CO: [(CH₂O), CO and CH₂OH] (D) H₂CCROH and C₂H4; [(CH₂O), CO and CH₂OH] R-CH₂-CH₂ - CH₂ - COH H₂C=CR = CROH and H₂C = CH₂ C₂H403 and CH4 P.T.O.arrow_forward
- (a) Account for the following :(i) Electrophilic substitution reactions in haloarenes occur slowly.(ii) Haloalkanes, though polar, are insoluble in water.(b) Arrange the following compounds in increasing order of reactivity towards SN2 displacement:2-Bromo-2-Methylbutane, 1-Bromopentane, 2-Bromopentanearrow_forwardGive reasons: (i) C—Cl bond length in chlorobenzene is shorter than C—Cl bond length in CH3—Cl.(ii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride.(iii) SN1 reactions are accompanied by racemization in optically active alkyl halidesarrow_forwardCompound 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.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_forwardAn unknown alcohol with a molecular formula of C7H14O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled, two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original un-known alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.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
- Arrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3arrow_forward5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.arrow_forwardBoth cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH3)3 as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanoleliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.arrow_forward
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