2.The following reaction results in two possible carbocation rearrangement products, each of which can becharacterized by a change in the ring size. Give structures for both products. There is no need to show themechanism of the reaction.HCI (conc)

Answered: HCI (conc) it

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Chemistry

HCI (conc) it

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.SE: Something Extra

Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...

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A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under thesame conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C.Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structuresof A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions
Compounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle (Previous Next
f) Alkene X can be decomposed with hydrogen peroxide catalyzed by sodium tungstate to substance Q. This can be further degraded by iodoform reaction to substance R. Give the structures of substances Q and R. Xx S Na₂WO4 H₂O2 Q (C9H1603) 1: NaOH, 1₂ 2: H+ P₂O5 teplo - CHI3 R (C8H1404) P₂O5 teplo T g) The preparation of substance Q from substance X using hydrogen peroxide is a redox reaction. Identify the reductant and oxidant in this reaction, write the formal oxidation number to the atoms where it changes during the reaction and calculate the reaction. h) Substances Q and R undergo a reaction with phosphorous oxide under heating to form various products T and S. Determine the structure of substances T and S if you know their H NMR : 1H NMR (S): 2.2 (t, 2H); 1.8 (t, 2H); 1.3 (s, 6H). 1H NMR (T): 4.6 (d, 1H); 4.3 (d, 1H); 2.2 (t, 2H); 1.5 (t, 2H); 1.3 (s, 6H).
C(CH3)3X +H20 where (X-F, CI, Br, I) give reaction with each of halogen as well determine with which halogen substitution reaction is more favorable and feasible and give reason of its feasibility? C(CH3)3OH
Q3. 2-Bromopentane, when treated with ‎ alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant? ‎ Q4 Which statement below about Sn1 reactions is incorrect? (A) SN1 reactions are stepwise and have intermediates. (B) The slow step in a SN1 reaction is formation of the carbocation intermediate. (C) SN1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a SN1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates.
Q3. 2-Bromopentane, when treated with alcoholic KOH yields a mixture of three alkenes A, B and C. Identify A, B and C. Which is predominant? Q4 Which statement below about Sn1 reactions is incorrect? (A) Syl reactions are stepwise and have intermediates. (B) The slow step in a Sy1 reaction is formation of the carbocation intermediate. (C) Sx1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a Sy1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates. Q5 would you rank their likely order of formation from most likely to least likely? If the alkenes below were possible products of an elimination reaction, how R R R R R R R R II II IV V (А) І, V, IШ, П, IV (В) IV, II, П, І, V (С) V, I, I, П, IV (D) IV, I, Ш, І, V (E) II, П, І, V, IV
2. (a) Give the product of the following reaction: Br t-BUOK (b) Using the FMOS of the reacting partners explain why this reaction is expected to occur simply on heating, in the absence of light. (c) Specify the preferred stereoisomer and explain why it is preferred.
A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.
Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry (g) 1) BH3. THF 2) H202, OH (h) 1) Hg(OАC), H,о 2) NABH4
[IV2] Instructions: Follow the flow of electrons indicated by the curved arrows in each of the following reactions, and predict the products that result: (refer to the photo below)
4. The reaction of the epoxide with methoxide produces one of the two constitutional isomers of methoxy-methylcyclopentanol shown below. Write the steps in the mechanism for this process. Be sure to show the following: (1) the structure of any intermediates that are formed during the mechanism, (2), what, if anything, is added or lost during each step of the mechanism, (3) any non-zero formal charges found on the structures that you write. REMEMBER: You may not use any materials except those that are given in the equation. OH H₂C * F OH NaOME/McOH