Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 11, Problem 57P
Interpretation Introduction
Interpretation:
The mechanism for the epioxidation of
Concept introduction:
Epoxidation is a process in which an
Epoxides are also known as cyclic ether, which are more reactive than usual ethers because of the strain applied by the chain of three atom, that is,
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(c) Alkenes can be transformed into epoxides by an epoxidation reaction. If the following hexenes are all subjected to an epoxidation reaction, which one would give an achiral epoxide? Explain your answer.
1-hexene
cis-2-hexene
trans-2-hexene
cis-3-hexene
trans-3-hexene
Elimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene
constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene
products. Offer an explanation for this difference.
Two isomeric materials are available for your use. They are:
A. 2-methyl-2-pentene (CH3)2C=CHCH2CH3B. 2-ethyl-1-butene (CH3CH2)2C=CH2
Give the name/s only (structures not required) of the product for the reaction of (i) A and (ii) B with the reagents listed below. Your answers should be given using A1 -A10 and B1-B10 as indicators.Eg. the product for your first reaction should be stated as A1 = name of product etc.
8. Peroxyacetic acid
9. Br2, 600 degrees Celsius
H2/ Li/ NH3
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - PRACTICE PROBLEM
11.8 Show how you would prepare...Ch. 11 - PRACTICE PROBLEM
11.9 Write structures for...Ch. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - 11.33 What compounds would you expect to be formed...Ch. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - 11.37 Outlined below is a synthesis of the gypsy...Ch. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Prob. 40PCh. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 43PCh. 11 - 11.44 Write a mechanism that accounts for the...Ch. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Prob. 47PCh. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Prob. 53PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 56PCh. 11 - Prob. 57PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...Ch. 11 - 11.1 Which set of reagents would effect the...Ch. 11 - Prob. 2QCh. 11 - 11.3 The following compounds have identical...Ch. 11 - Complete the following synthesis:Ch. 11 - Two configurations can actually be envisioned for...
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- Two isomeric materials are available for your use. They are: A. 2-methyl-2-pentene (CH3)2C=CHCH2CH3B. 2-ethyl-1-butene (CH3CH2)2C=CH2 Give the name/s only (structures not required) of the product for the reaction of (i) A and (ii) B with the reagents listed below. Your answers should be given using A1 -A10 and B1-B10 as indicators.Eg. the product for your first reaction should be stated as A1 = name of product etc. HBr HOBr Ozone (O3)/Zn B2H6/H2O2 N-bromosuccinimide KMnO4/ OH- Hg (OAc)2 CH3CO2OH (Peroxyacetic acid) H2/ Pd H2/Li/NH3arrow_forwardBromine reacts with alkenes in methanol according to the equation (see image 1). When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield) a) Which of the following is the structure more reasonable for this compound? (see image 2) b) Explain your reasoning through a corresponding mechanismarrow_forwardA hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.arrow_forward
- Choose the correct answer lettered A-E and explain briefly with illustrations the chemistry behind the answer Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products. 1.Predict the products that would be formed from such a reaction A.1-pentene (80%) and 2-pentene (20%)B.1-pentene (20%) and 2-pentene (80 %)C.1-pentene (50 %) and 2-pentene (50 %)D.1-pentene (0 %) and 2-pentene (100 %)E.1-pentene (100 %) and 2-pentene (0 %) 2.What reaction pathway is followed by the reaction above?A.E2 dehydrohalogenation B.E1 dehydrohalogenationC.SN1 dehydrohalogenationD.SN2 dehydrohalogenationE.A mixture of E1 and E2 pathways 3.What is responsible for the formation of different products (major and minor).A .The different activated complex involved in the mechanism.B.Bimolecular Nucleophilic substitution reaction C.Bimolecular Elimination reaction D.The presence of sodium ethoxideE.The…arrow_forwardNn.84. Subject :- Chemistryarrow_forwardI cannot figure out this question about ozonolysis of an alkene? There are two double carbon bonds to choose from on the ring, so how do we know what is being acted on? (if that makes sense) Thank you!arrow_forward
- Write a mechanism for the acid-catalysed addition of water to: (b) 3-hexene.arrow_forwardChoose from the options A-E and explain briefly by illustrations the chemistry behind each answer. Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products. 1.Predict the products that would be formed from such a reaction A.1-pentene (80%) and 2-pentene (20%)B.1-pentene (20%) and 2-pentene (80 %)C.1-pentene (50 %) and 2-pentene (50 %)D.1-pentene (0 %) and 2-pentene (100 %)E.1-pentene (100 %) and 2-pentene (0 %) 2.What reaction pathway is followed by the reaction above?A.E2 dehydrohalogenation B.E1 dehydrohalogenationC.SN1 dehydrohalogenationD.SN2 dehydrohalogenationE.A mixture of E1 and E2 pathways 3.What is responsible for the formation of different products (major and minor).A.The different activated complex involved in the mechanism.B.Bimolecular Nucleophilic substitution reaction C.Bimolecular Elimination reaction D.The presence of sodium ethoxideE.The hybridisation…arrow_forwardWrite the equations for the preparation of 1-bromobutane from :(i) 1-butanol (ii) but-l-enearrow_forward
- 4. A certain endothermic reaction X carried out room temperature (273K) has an enthalpy change of 20 Kcal/mol and an entropy change of 10 Kcal/K/mol. i) Calculate the Gibbs free energy (AG) of this reaction. ii) Is this reaction spontaneous or non-spontaneous? Give a reason for your answer 5. Thiomethane reacts with compound A via an SN1 reaction. Complete its reaction equation below. ii) SH Compound A ii) Draw the mechanism of reaction for this reaction. 6. Butyl Chloride undergoes an elimination reaction when reacted with sodium ethoxide to form butene. The reaction equation is given below with two reaction products A and B. low inevloa CI noitsups p *OEt B Which is the major product, and which is minor product. (Hint: Look up how the size of the base affects the elimination reaction product) Give a reason for your answer.arrow_forwardSome 2-methyl-2-butene may be produced in the reaction as a by-product. Give a mechanism for its production.arrow_forwardPlease don't provide handwriting solutionarrow_forward
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