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- 6. Which of the following alcohols is oxidized to a ketone by chromic acid? I. II. III. I. II. OH III. OH CH₂OH 7. What are the major organic products when the following molecule is treated with ozone, and then with Zn/H2O? CH₂ Yu A. I B. II C. III D. IV E. V ,COH O IV. H-C-H IV. COOH V. 2 CH₂O CH₂OH CH₂ C-CH3 OH V. -OH Jº. n&on но- -он Y. A. I B.II C.III D.IV E. V 8. What compound results when 1-heptyne undergoes ozonolysis? A. heptanal B. 2-heptanone C. heptanoic acid D. hexanoic acid and CO2 E. 1-heptanol67. The structure of the compound produced by this reaction: + B2 is 68. The primary reaction product of the reaction given be low is CH2-CH=CH, + H20 When a straight chain a lcohol is reacted with H2504, H3C-CH2-CH2-CH=CH, and H3C-CH2-CH CH-CH3 are both formed. The structure of the original alcohol was 69.CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:
- 5.Synthesis. Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. Br CH 3 Br CH36. Give the major products for the following reactions. B THF, 65 °C 1. MeOH Na OH, H202 H2O/OH 2.Complete the reaction by providing the starting material/reagent/products. Match each item to a choice: CI Cl₂ FeCl3 HO OH NO₂ for HO NO₂ O SO3 conc. H₂SO4 NO₂ KMnO4 H₂O
- 10. Terpene is a class of naturally occurring molecules, found in many essential oils from plants, that share the same alkene features. All terpenes have a similar 5 carbon unit that includes an alkene thought to be biologically synthesized from the molecule isoprene. All terpenes are biosynthesized from molecules with the good leaving group: pyrophosphate (OPP). Loss of this OPP leads to the formation of a resonance stabilized carbocation. The new carbocation can undergo a nucleophilic attack from a T-bond as seen in acid-catalyzed hydration and hydrohalogenation, forming a new carbocation. This new carbocation can undergo an E1 reaction to form a new alkene. Add the curved arrows of the following reaction. hopp COPP D 5 R-carvone (spearmint oil) - Q Search 40 6 & COPP 1 COPP COPP33. Consider the reaction scheme below: CH;CHO A CH;MgBr D B CH,CN CH3COOH Y 1. Dry ether 2. H30* E CH;COOCH2CH3 CH3COCI NH3 a) Draw the structural formulae for X, Y and Z b) State the reagent(s) and condition(s) for A, B, C, D and E11. Provide the major organic product of the reaction shown below. I. LIAIH, 2 H,0 co,H 12. Provide the major organic product of the following reaction. -NH2 acetic anhydride 13. Provide the major organic product of the following reaction. CO,H SOCI, 14. Provide the major organic product of the following reaction. OH conc. KMNO4, heat
- 40. Deuterium oxide, D20, is water that contains the stable hydrogen isotope 2H, usually shown as D. When dissolved in deuterium oxide, ethanol undergoes the following reaction: * CH3CH2OH + D½0 → CH;CH2OD + HOD What is the best way of showing that this reaction has occurred? A. By testing the product with phosphorus pentachloride and not getting steamy fumes. B. By determining the mass spectrum of the mixture and showing peaks at m/z values of 20 and 46. C. By fractionally distilling the mixture and determining the amount of CH3CH2OD using a Geiger counter. D. By determining the mass spectrum of the mixture and showing peaks at m/z values by 19 and 47. A В O D1. Draw structure of the products of the reactions I KMN04 Acetone O NAOH H. EtOH H. КОН? 2 Ethanol glish (U.S.)A compound X of molecular formula C7H14 when hydrogenated produces 2,4-dimethylpentane and when hydroborated the obtained alcohol is 2,4-dimethyl-1-pentanol. a. What is the structure of X? b. If X is reacted with H2O catalyzed by H2SO4, what product is obtained? Write the structure, give the name, and write the complete mechanism, step by step of this reaction, in such a way as to explain the formation of the compound (DO NOT FORGET THE CORRECT USE OF ARROWS!).