Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 10, Problem 10.47SP
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 decolorizes two -equivalents of Br2 to give F (C10H16Br4). 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.
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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.
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.
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.
Chapter 10 Solutions
Organic Chemistry (9th Edition)
Ch. 10.3A - Prob. 10.1PCh. 10.3B - Give both the IUPAC name and the common name for...Ch. 10.3B - Prob. 10.3PCh. 10.3C - Give a systematic (IUPAC) name for each diol. a....Ch. 10.4B - Predict which member of each pair will be more...Ch. 10.4B - Dimethylamine (CH3)2NH, has a molecular weight of...Ch. 10.6A - Prob. 10.7PCh. 10.6A - Prob. 10.8PCh. 10.6C - A nitro group (NO2) effectively stabilizes a...Ch. 10.6C - Prob. 10.10P
Ch. 10.8B - Prob. 10.11PCh. 10.8B - Prob. 10.12PCh. 10.9A - Prob. 10.13PCh. 10.9B - Prob. 10.14PCh. 10.9C - Show how you would synthesize each tertiary...Ch. 10.9D - Prob. 10.16PCh. 10.9D - Show how you would add Grignard reagents to acid...Ch. 10.9D - A formate ester, such as ethyl formate, reacts...Ch. 10.9E - Prob. 10.19PCh. 10.9E - In Section9-7B, we saw how acetylide ions add to...Ch. 10.9F - Prob. 10.21PCh. 10.10A - Prob. 10.22PCh. 10.10B - Prob. 10.23PCh. 10.11B - Predict the products you would expect from the...Ch. 10.11B - Prob. 10.25PCh. 10.11B - Prob. 10.26PCh. 10.12 - Prob. 10.27PCh. 10.12 - Prob. 10.28PCh. 10.12 - Authentic skunk spray has become valuable for use...Ch. 10 - Give a systematic (IUPAC) name for each alcohol....Ch. 10 - Give systematic (IUPAC) names for the following...Ch. 10 - Draw the structures of the following compounds...Ch. 10 - Predict which member of each pair has the higher...Ch. 10 - Predict which member of each pair is more acidic,...Ch. 10 - Predict which member of each group is most soluble...Ch. 10 - Draw the organic products you would expect to...Ch. 10 - Prob. 10.37SPCh. 10 - Show how you would synthesize the following...Ch. 10 - Show how you would use Grignard syntheses to...Ch. 10 - Show how you would accomplish the following...Ch. 10 - Show how you would synthesize the following: a....Ch. 10 - Complete the following acid-base reactions. In...Ch. 10 - Prob. 10.43SPCh. 10 - Prob. 10.44SPCh. 10 - Geminal diols, or 1,1-diols, are usually unstable,...Ch. 10 - Vinyl alcohols are generally unstable, quickly...Ch. 10 - Compound A (C7H11Br) is treated with magnesium in...Ch. 10 - Prob. 10.48SPCh. 10 - Prob. 10.49SPCh. 10 - Prob. 10.50SPCh. 10 - Prob. 10.51SPCh. 10 - Prob. 10.52SPCh. 10 - Prob. 10.53SPCh. 10 - Prob. 10.54SPCh. 10 - Prob. 10.55SPCh. 10 - Prob. 10.56SPCh. 10 - Show how this 1 alcohol can be made from the...Ch. 10 - Prob. 10.58SPCh. 10 - Prob. 10.59SPCh. 10 - Prob. 10.60SP
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- 5. 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_forwardCompound 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 throughoutarrow_forwardCompound 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_forward
- 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.arrow_forwardUsing the normal/primary isomer of C4H10O, treat it with conc.H2SO4 and heat to produce A. Treatment of A with HCl/H2O gives B and with cold KMnO4/ OH- gives C . Give the name and structures of A, B and C Treatment of A with Hot KMnO4/OH- gives D followed by acidification of the mixture to give E. What is D and E ?arrow_forwardCompound A has the formula C9H19Cl. B is a C9H19Br compound.A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products.C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane.Addition of HCl to C yields A as the major product.Propose structures for A and B.arrow_forward
- 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. Can be more than one answerarrow_forwardCompound 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_forwardCompound P (C2H4) which is an alkene undergoes reaction with HCl to produce compound Q (C2H5Cl). Reaction of compound Q with benzene in the presence of AlCl3 as catalyst produces compound R. Then, nitration of compound R in the presence ofnH2SO4 produces two compounds, S and T. But when compound R is reacted with a hot acidified solution of alkaline KMnO4 gives compound U. Deduce the structure of compounds P to U.arrow_forward
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