Compound (2E,4Z,6Z,8E)-2,4,6,8-decatetraene has been cyclized to give 7,8-dimethyl- 1,3,5-cyclooctatriene. Predict the manner of ring-closure-conrotatory or disrotatory-for boththermal and photochemical reactions and predict the stereochemistry of the product in eachcase. Show the outermost molecular orbital cyclizaion.

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Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Predict the organic products of the following reaction. Show stereochemistry clearly. The (R) or (S) designation for each stereocenter carbon atom is specified adjacent to the answer box, please draw the products accordingly. X H KMnO4 (aq) KOH, cold (3R, 4S) (3S, 4R)
Using one or more of the following compounds as starting materials or products illustrate, with an example, each of the following type of pericyclic reactions. Your answer should include curved arrow mechanisms. (i) a disrotatory thermal electrocyclic reaction (ii) a conrotatory photochemical electrocyclic reaction (iii) a [4+2] cycloaddition (iv) a [3,3]-sigmatropic rearrangement
Alpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: 0 || CH3C-CH 0 || ● Propose a structure for alpha-phellandrene. (+ || HCCH₂CHCH I CH(CH3)2 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. n [ ]# ?
Rearrange the compounds of each of the following sets in increasing order of reactivity towards SN2 displacement: (i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane (ii) l-Bromo-3-methylbutane, 2-Bromo-2-methyl butane, 3-Bromo-2- Methylbutane. (iii) 1 -Bromobutane, l-Bromo-2,2 -dimethylpropane, 1 -Bromo-2 -methyl butane
(a) Write the products of following reactions. Give mechanism with proper stereochemistry? (2 x 2.5 = 5) (ii) Me Δ Δ CN
Predict the major organic product for the following reaction. You do not need to account for stereochemistry, but be sure your answer accounts for regiochemistry where appropriate. Assume cis conformation of the diene. HC=CH Product?
Calculate the AH° for the following reaction step. What can you say regarding the pos- sibility of bromination at a vinylic hydrogen? CH,=CH, Br- → CH,=CH. HBr
1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.
The primary amine isoamylamine (3-methylbutylamine) occurs naturally in a number of fruits and is used as a food flavouring: (CH3),CHCH,CH,NH, 3-methylbutylamine Suggest two ways in which it can be synthesised from suitable organic precursors. Note that only one of the two methods you propose may involve the reduction of another nitrogen containing compound. In each case, you should indicate what starting material and other reagents are needed, though details of precise experimental conditions or reaction mechanisms are not required.
Provide the products of the reaction of 1-propene with HBr in the presence and absence of peroxide. Explain the mechanism of the formation of the products in detail
Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)
(c) You conducted an experiment involving a hydrohalogenation reaction with starting material A and HBr. Product C was obtained as the major product of the reaction instead of the regioisomer product B which you expected. CH3 CH3 CH3 Br Br + HBr Product B Starting material A Product C (i) Suggest a detailed reaction mechanism to explain the formation of the major product C. (ii) Briefly explain why this unexpected major product C predominated in your reaction. Question 1 Continued (iii) 1,2-elimination of HBr from product C yields a mixture of two alkenes. Draw the structures of the two alkene products and briefly explain using Zaitsev's rule which alkene is the major one.

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