Both 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
Want to see the full answer?
Check out a sample textbook solutionChapter 11 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Additional Science Textbook Solutions
Chemistry & Chemical Reactivity
General Chemistry: Principles and Modern Applications (11th Edition)
Chemistry: An Introduction to General, Organic, and Biological Chemistry (12th Edition) - Standalone book
Organic Chemistry
CHEMISTRY-TEXT
General, Organic, & Biological Chemistry
- (b) (1-chloromethyl)cyclopentane, CeH11CI reacts with aqueous sodium hydroxide, NaOH to produce a primary alcohol AA. When CeH11Cl is added with magnesium, Mg in ether, an organometallic compound BB is formed. When compound BB reacts with ethanal, CH3CHO, a secondary alcohol cCis formed. The molecular structure of CeH11Cl is given below. (1-klorometil)siklopentana, CoH1,CI bertindak balas dengan akues natrium hidroksida, NaOH bagi menghasilkan satu alkohol primer AA. Apabila CeH11CI ditambah dengan magnesium, Mg dalam eter, sebatian organologam BB terbentuk. Apabila sebatian BB bertindak balas dengan etanal, CH;CHO, satu alkohol sekunder CC dihasilkan. Struktur molekul bagi CsH11CI diberikan di bawah. .CI (1-chloromethyl)cyclopentane (i) Draw the structural formula for compound AA through Cc. Lukiskan formula struktur bagi sebatian AA sehingga C. (ii) What is the type of reaction to produce compound AA? Apakah jenis tindak balas untuk menghasilkan sebatian AA?arrow_forwardA compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.arrow_forwardHydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?arrow_forward
- An 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 unknown alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.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 unknown alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.arrow_forwardWrite structural formulas for all ketones with the molecular formula C6H12O and give each its IUPAC name. Which of these ketones are chiral?arrow_forward
- On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) yielded a mixture of two alkenes B and C, each having the molecular formula C7H14. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.arrow_forwardMethyl acrylate (H2C=CHCO2CH3) reacts with 1,3-cyclopentadiene to give a mixture of two products. Write structural formulas for both and predict which one predominates.arrow_forward1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12. (a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W. (b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial, O=CH—CH2CH2—CH=O. Draw the structure of X.arrow_forward
- Three constitutional isomers of molecular formula C 5H 8O can be converted to 1-pentanol (CH 3CH 2CH 2CH 2CH 2OH) on treatment with two equivalents of H 2 in the presence of a Pd catalyst. Draw the structures of the three possible compounds, all of which contain a carbonyl grouparrow_forwardDevelop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentanearrow_forwardAn 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.arrow_forward