Concept explainers
(a)
To determine: The mechanism to show which three fluoroalkenes are formed by the reaction of
Interpretation: The mechanism to show which three fluoroalkenes are formed by the reaction of
Concept introduction: The elimination reaction is the organic reaction in which two substituents are removed from the organic molecule in one step or two steps. The two mechanisms of the elimination reaction are E1 and E2 mechanism.
E1 mechanism is carried out with
The
(b)
To determine: The mechanism to show the formation of
Interpretation: The mechanism to show the formation of
Concept introduction: In
In
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Organic Chemistry (9th Edition)
- 3. Write down the mechanism for the following reaction and predict which of the two possible products will be formed in the greatest yield (2nd and 3rd carbocation). Write down the structures of the two possible products and explain your answer. CH3CH = CHCH2 CH2 CH3 + HBrarrow_forwarda. Identify the substitution products that form when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water. b. Explain why the same products are obtained when 2-chloro-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forward
- Substitution and Elimination (Please draw the structures involved in the reactions) A. Which will react more rapidly via SN1? 1-bromo-2,2-dimethylpropane or 2-bromo-2- methylbutane? Explain. B. Which will react faster via SN2? 1-chlorocyclohexane or 1-chloro-1-methylcyclohexane? Explain.arrow_forward43. Identify the reagent that will produce the following brominated product in greatest amount. Br A. Br₂/uv ? B. Br2/FeBr3 C. NBS D. Br2/CC14 44. Under acidic condition, which of the following compounds can not be oxidized by KMnO4. A. toluene B. 2-butene C. methylcyclohexane D. 2-butynearrow_forwardThe reaction below involves 2-chloropentane reacting with water. The product of this reaction is 2-pentanol. What would be the stereochemical result of the product? CH3 OH c CH;CH2CH3 H20 H. a. 100% R b. 100% S O C. ~50% R, ~50% Sarrow_forward
- 43. Identify the reagent that will produce the following brominated product in greatest amount. Br A. Br2/uv B. Br2/FeBr3 C. NBS D. B12/CC14 44. Under acidic condition, which of the following compounds can not be oxidized by KMnO4. A. toluene B. 2-butene C. methylcyclohexane D. 2-butyne 45. What alkene product can be produced from the reaction of 2-hexyne with Lindlar's catalyst? A. cis-2-Hexene B. trans-2-Hexene C. Hexane D. A and Barrow_forwardDraw a reaction mechanism illustrating the transition state structure and stereochemistry of the resulting product (if any).a. (R)-2-bromobutane + -OCH3 → (SN2)b. (S)-3-bromo-3-methylhexane + methanol → (SN1)c. 2-Chloro-2-methylhekxane + -OH → (E1)arrow_forward1. Theoretical questions Use the following E1 reaction to answer the theoretical questions. H,SO, 4,0 217 C 231 C a. Propose a mechanism for the formation of each product. b. A carbocation rearrangement must occur to form product C. Why is this carbocation rearrangement favored? c. Rank the products in order of increasing stability of the alkene.arrow_forward
- Which stereoisomer would be produced from the reaction of trans-2-butene with OsO4 followed by H2O2? A. 2S,3S- diol and 2R, 3R-diol B. 2S,3R-diol and 2R,3S-diol C. 2S,3S-diol only D. 2R, 3R-diol only E. 2S,3R-diol onlyarrow_forwardCompare the cis and trans isomers of 1-bromo-4-tert-butylcyclohexane upon reaction with sodium ethoxide in ethanol. Select all answers that apply. The reaction is first order in substrate and first order in ethoxide. a. The product is an alkene. b. The cis isomer reacts more rapidly. C. The reaction occurs in two distinct steps. d. The product is racemic. е.arrow_forward4. Which of the following reactions is NOT a method of preparation of alkylhalide? A. addition of halogens to alkenes B. replacement of the -OH in alcohol by a halide C. dehydrohalogenation of hydrocarbon D. addition of hydrogen halide to alkene 5. In SN₂ reaction of alkylhalide(substrate) with NaOH(nucleophile), the rate of the reaction is tripled if the concentration of: A. Substrate and nucleophile are both doubled B. Nucleophile is decreased by 1/3 and substrate doubled C. Substrate is tripled and nucleophile doubled D. Nucleophile is tripled 6. Arrange the following alkylhalide in order of decreasing reactivity in an SN₁ reaction: I. CH3CH(Br)CH₂CH3 A. I>II>III>IV II. CH3CH(C1)CH₂CH3 III. CICH₂CH₂CH₂CH3 IV. (CH3)2C(Br)CHCH3 D. IV>II>I>III B. IV>III>II>I C. IV>I>II>IIIarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning