Starting from a terminal alkene R-CH=CH2, is there any advantage in using the two-step protocol (halohydrin formation + intramolecular williamson) over the direct epoxidation procedure? HINT: check for other reactions of MCPBA. Is this also an oxidant for other funcional groups? WHich ones? would a chemoselectivity problem be expected if those functional groups were also present during the epoxidation reaction?

Starting from a terminal alkene R-CH=CH2, is there any advantage in using the two-step protocol (halohydrin formation + intramolecular williamson) over the direct epoxidation procedure? HINT: check for other reactions of MCPBA. Is this also an oxidant for other funcional groups? WHich ones? would a chemoselectivity problem be expected if those functional groups were also present during the epoxidation reaction?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter16: Synthesis Workshop 1

Section: Chapter Questions

Problem 10CTQ

See similar textbooks

Similar questions

During the workup portion of the reaction of alkenes with HBr as described in the experiment provided, a student transferred the reaction mixture to a separatory funnel, rinsed the reaction flask with diethyl ether, and added the ether rinses to the separatory funnel. The student then added sodium bicarbonate to the separatory funnel. Extremely vigorous bubbling occurred. What did the student do wrong? Can they still isolate the product? If so describe the next steps the student should take to isolate the product.
Help ASAP Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Do this by writing all the possible resonance forms for methoxybenzene, including the hybrid. Based on your structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack; (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
E. J. Coreys 1964 total synthesis of -caryophyllene (essence of cloves) solves a number of problems of construction of unusual-sized rings. The first step uses an efficient photochemical [2 + 2] reaction. The desired stereochemistry and regiochemistry had been predicted based on model reactions. (a) [2 + 2] Reactions are quite common in photochemical reactions. Would this reaction be predicted to occur in the ground state? The next steps follow. Basic alumina is a chromatography support that will often act as a base catalyst. (b) What is the mechanism of the first step? (c) What is the mechanism of the second step? (d) Look at later steps in the synthesis. Does the stereochemistry of the added carbomethoxy group matter? The next steps are shown here. (e) What is the structure of compound (A)? (f) Give a mechanism for the formation of the cyclized product. (g) Give a mechanism for the first step. Hint: Attack on the lactone carbonyl may be the first step. (h) Give a structure for product (B). The following two steps are next. (i) Show the reactions of (B). (j) Write a mechanism for the ring-opening reaction. Hint: Note the presence of an acidic proton and a good leaving group in the molecule. The synthesis was completed by the following steps. (k) What is (C)? (l) What reagents would you use for these transformations?
I recovered 3 mL of cyclohexene, how many grams of water was produced in the reaction please show how? Cyclohexanol can attack the carbocation intermediate formed during the synthesis of cyclohexene. Draw this side product with the molecular formula C12H22O. Please ASAPPPP you guys didn't answer the last one
(A) Show the steps in the mechanism for the conversion of butane to 2-bromobutane using Br2 in the presence of UV light. Be sure to identify initiation, propagation, and termination steps. (B) Starting with toluene (methylbenzene) and any other inorganic or organic reagents or catalysts, show a series of reactions (with reagents) for the synthesis of benzyl ethanoate (benzyl acetate).
A student was about to turn in the products he had obtained from the reaction of HI with 3,3,3-trifluoropropene when he realized that the labels had fallen off his flasks and he did not know which label belonged to which flask. His friend reminded him of the rule that says the electrophile adds to the sp2 carbon bonded to the most hydrogens. In other words, he should label the flask containing the most product 1,1,1-trifluoro-2-iodopropane and label the flask containing the least amount of product 1,1,1-trifluoro-3-iodopropane. Should he follow his friend’s advice?
Does the data provide evidence for the claim that the reaction of Br2 with alkenes proceeds via anti‐addition? The mleting point of the product was found to be 234.5-235.5C chemical reaction: trans-stilbene+pyrimindine tribromide --->acetic acid 1,2-di bromo-1,2-diphenylethane product was trans-1,2-dibromo-1,2-diphenylethane
Show the products generated from the HBr reaction with each of the following alkenes, not forgetting to indicate which is the majority product.
Box 31-33 .Unless otherwise directed, show only the major product. For reagent or reactant questions, fill in the missing information.
thanks. multiple choice: 1. Which of the following is true regarding an SN1 reaction? a. It would be faster at 25 ̊ than 50 ̊ b. It would be faster in ethanol than in pentane c. Keeping the moles of reactants constant but doubling the quantity of solvent would decrease the rate by a factor of 4. d. Stereochemical inversion occurs exclusively 2. Which of the following statements is true? a. The rate determining step is always the last step in a reaction mechanism. b. The stability/reactivity principle says that the more stable of two chemicals will be more reactive c. The reactivity/selectivity principle says that the more reactive of two chemicals will be less selective. d. The activation barrier for a reaction is the difference in energy between reactants and final products. 3. Which of the following statements is FALSE? a. Optically active solutions always contain chiral molecules. b. Two diastereomers always have identical melting points c. Optically…
Draw the product of an SN2 reaction shown below. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore inorganic byproducts.
In the chemical reaction between 1-Bromobutane and ethanolic silver nitrate solution, a precipitate is barely formed. Using the skeletal structures of the molecules, write out the skeletal structure of each reaction (don't include the mechanism). Identify what the nucleophile is in each type of reaction, especially the SN1 reaction. Explain the reactivity of each electrophile/substrate in terms of whether they are tertiary, secondary, primary, etc. for each reaction. Include the overall chemical reaction.