Practice Problem 7.16
Acid-catalyzed dehydration of neopentyl alcohol,
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- 2. (a) (b) OUTLINE, using suitable mechanisms, how each of the following conversions is achieved. In each case, you should indicate the reagents to be used and show ALL intermediate compounds. Each arrow may represent one or more than one step. CH3CH₂Br (C6H5)3P CHCH3 H CH3 ——-||- H- (C₂H₂)₂N- H H CH,CH,CHO -CHO H₂C CH3 CHCH3arrow_forward(c) A series of dialkyl ethers react with excess hydrogen bromide, with the following results. Analyze the ether in each case and write out the complete chemical equations. (1) Ether gives a mixture of bromocyclopentane and 1-bromoethane. (ii) Another ether gives one mole of 1,5-dibromopentane per mole of ether.arrow_forwardGive the reaction mechanism showing all possible products for the following reactions: (a) Reaction of 1-propene with hydrogen bromide, HBr (9) (b) Reaction of ethene with bromine, Br2 (1)arrow_forward
- (c) The structures of lycopene, beta-carotene and retinol are shown below. Lycopene Beta-carotene H3C CH; CH3 CH3 OH Retinol (vitamin A) CH3 Using appropriate reaction mechanisms: (i) Show how lycopene is converted into beta-carotene. (ii) Briefly explain how retinol is formed from beta-carotene.arrow_forward(a) Illustrate the following name reactions giving a chemical equation in each case :(i) Clemmensen reaction (ii) Cannizzaro’s reaction(b) Describe how the following conversions can be brought about :(i) Cyclohexanol to cyclohexan-1-one (ii) Ethylbenzene to benzoic acid(iii) Bromobenzene to benzoic acidarrow_forwardStarting exactly with any acid chloride with exactly with 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules: (a) 2,6-dimethyl-4-heptanone (b) 4-propyl-4-octanolarrow_forward
- Suggest suitable reagent(s) and conditions to perform the transformations (i) - (iv) below. Sometimes more than one step may be required. Consideration of stereochemistry and curved arrow mechanisms are not required. (i) (ii) (iii) MeO₂C CO₂Me D D [D = ²H] HO₂C OH OMearrow_forwardDraw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forwardG.62.arrow_forward
- 1. Outline mechanisms for the following addition reactions. (a) (b) ICI (c) HBr HI 2. Provide mechanistic explanations for the following observations (a) HCI CI (b) HCI 3. Treatment of 3-methylcyclohexene with HCl yields two products, 1-chloro-3- methylcyclohexane and 1-chloro-1-methylcyclohexane. Draw a mechanism to explain this result. 4. Addition of HBr to which of the following alkenes will lead to a rearrangement? a. CH;=C(CH,)CH,CH, b. CH3CH=CHCH,CH; c. CH3CH=CHCH(CH,),arrow_forwardWhen heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produces a mixture of two alkenes B and C, each of which has the molecular formula C7H14 . Catalytic hydrogenation of major isomer B or minor isomer C produces only 3-ethylpentane. Suggest the structures and mechanisms for compounds A, B, and C consistent with these observations.arrow_forwardOn 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.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning