Concept explainers
Interpretation: The given question stated that unknown X,
Concept introduction: Hydrogenation is a chemical process in which
Ozonolysis is the oxidative cleavage of the double bond, where
To determine: The structure of X, Y, and Z and the aspect of the structure of X that is still unknown.
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Organic Chemistry (9th Edition)
- 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 throughoutarrow_forwardCompound 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_forward18. 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 followed by hydrolysis gives D (C10H180). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizes two equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess of H₂ and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F by showing clearly all the reactions involved.arrow_forward
- Unknown X, C5H9BrC5H9Br, does not react with bromine or with dilute KMnO4KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5H8C5H8. Unlike X, Y decolorizes bromine and changes KMnO4KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis-reduction of Y gives dialdehyde Z, C5H8O2C5H8O2. Part A Propose consistent structures for X, Y, and Z.arrow_forwardTreatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.arrow_forwardCompound A (C9H12) absorbs three equivalents of H2 on a Catalina reduction over a palladium catalyst to give propylcyclohexane. On ozonolysis, compound A give the two products shown below. On treatment with NH2 , NH3 followed by addition of 1_bromo4methylpentane, compound A gave a new hydrocarbon,B (c5H24 ). What are the structures of compound A and B?arrow_forward
- The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.arrow_forwardCompound 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.arrow_forwardCompound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over apalladium catalyst to give B (C9H18). On ozonolysis, compound A produced 3 products, C, Dand E which was a ketone identified as cyclohexanone. On treatment with NaNH2 in NH3,followed by addition of iodomethane, compound A gave new hydrocarbon, F (C10H14). Drawstructures of A, B, C, D and F.arrow_forward
- (S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C,HgO). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.arrow_forwardThe reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.arrow_forwardTreatment of compound A (C8H17Br) with NaOCH2CH3 affords twoconstitutional isomers B and C. Ozonolysis of B affords CH2=O and(CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 andCH3CH2CHO. What is the structure of A?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning