Concept explainers
Interpretation:
Given reaction of 2-metylpropene with CH3OH in the presence of H2SO4 catalyst yields methyl tert-butylether, CH3OC(CH3)3, by a mechanism analogous to that of acid catalyzed
Concept introduction:
In the presence of strong acids the double bond in alkene is protonated by the nucleophilic attack of the π electrons in double bond on the hydrogen of the acid. The carbonium ion obtained during the process is then attacked by the unshared pair of the electrons on oxygen in methanol to yield an intermediate which loses a proton to give the final ether as product.
To give:
The mechanism for each step of the reaction in which 2-metylpropene reacts with CH3OH in the presence of H2SO4 catalyst to yield methyl tert-butylether, CH3OC(CH3)3.
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Chapter 8 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
- Ethers (general formula R—O—R)have many important uses. Until recently,methyl tert-butyl ether (MTBE, right)was used as an octane booster and fueladditive for gasoline. It increases the oxy-gen content of the fuel, which reducesCO emissions. MTBE is synthesized bythe catalyzed reaction of 2-methylpropene with methanol.(a) Write a balanced equation for the synthesis of MTBE. (Hint:Alcohols add to alkenes similarly to the way water does.)(b) If the government required that auto fuel mixtures contain2.7% oxygen by mass to reduce CO emissions, how many gramsof MTBE would have to be added to each 100. g of gasoline?(c) How many liters of MTBE would be in each liter of fuel mix-ture? (The density of both gasoline and MTBE is 0.740 g/mL.)(d) How many liters of air (21% O₂ by volume) are needed at24C and 1.00 atm to fully combust 1.00 L of MTBE?arrow_forwardWhen 2-pentene is treated with Cl2 in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages).arrow_forwardQ2. Consider the nucleophilic substitution reaction between 3-chloro-3-methylpentane and the hydroxide ion: CI x + OH (a) Is the alkyl halide 1°, 2° or 3°? (b) Will the nucleophilic substitution reaction be S₁1 or S№2? (c) Give the substitution mechanism showing all full and partial positive and negative charges, electron movements using curved arrows.arrow_forward
- Bent (D) Trigonal pyramidal 5. A student wishes to prepare ethyl acetate from the reaction of ethanol and acetic acid. To be successful, this reaction requires (A) an acidic catalyst. (C) an oxidizing agent. (B) a basic catalyst. (D) a reducing agent. 6. Which alkyl halide reacts most rapidly with aqueous sodium hydroxide solution? (A) CH₂Cl (B) CH₂I (C) (CH3)3CCH₂Cl (D) (CH3)3CCH₂I 57. How many isomers are there with the formula C6H₁4?arrow_forwarddraw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocationarrow_forwardWhen 2-pentene is treated with Cl, in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages). CI OCH3 H,CO CI CI CI Cle CH;CHCHCH,CH, + CH;CHCHCH,CH3 + CH,CHČHCH,CH, CH;OH CH;CH=CHCH,CH, 50% 35% 15%arrow_forward
- Draw out the structures (condensed structural formulas) for the following reactions (reactants and products) and name the product formed. a) Hydrohalogenation of 1,3-dimethylcyclopentene with HBr Name product: b) Hydrogenation of 3,4-dimethylcyclobutene Name product: c) Hydration of 3-ethyl-2-pentene cturslomeo Name product: d) Alkylation of benzene with 2-chloropropane (isopropylchloride) Name product: e) Mono-halogenation of 2,2-dimethylbutane with Cl2 Name product:arrow_forwardDraw the products formed when the following alkynes are treated with each set of reagents: [1] H2O, H2SO4, HgSO4; or [2] R2BH followed by H2O2, −OH.arrow_forwardAcid-catalyzed hydration of 2-Methyl-1-butene yields two alcohols. The major product does not undergo oxidation, while the minor product will undergo oxidation. Explain why, by showing the structures of theproducts.arrow_forward
- Draw the organic product(s) formed upon the addition of HBr to (a) 2-methyl-2-pentene, (b) trans-2-hexene, and (c) 4-methylcyclohexene. How many regioisomers can be formed in each case?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_forwardAn important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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