Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 11, Problem 60P
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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Part A: Please explain in detail the mechanism of catalytic hydrogenation when applied to the reactants, (Z)-3-methyl-2-hexene and hydrogen gas, with the catalyst, Ni-C.
Part B: What are the product(s) of this reaction?
Bromine reacts with alkenes in methanol according to the equation
when this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound? Explain your reasoning through a corresponding mechanism.
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/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 - Prob. 9PPCh. 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 - Prob. 33PCh. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Predict the products from each of the following...Ch. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 42PCh. 11 - 11.43. A synthesis of the -receptor blocker called...Ch. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - 11.46. For each of the following, write a...Ch. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Outlined below is a synthesis of the gypsy moth...Ch. 11 - Prob. 54PCh. 11 - Prob. 55PCh. 11 - Prob. 56PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...
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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. 8. Peroxyacetic acid 9. Br2, 600 degrees Celsius H2/ Li/ NH3arrow_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_forwardYou are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.arrow_forward
- (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-hexenearrow_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_forwardChoose 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_forward
- X Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►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_forward4. 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_forward
- Write a mechanism for the acid-catalysed addition of water to: (b) 3-hexene.arrow_forwardUse line structures and write the mechanism for the first and second steps of the hydrobromination reaction of compound C in the presence of HBr to demonstrate that it is a regioselective reaction. Clearly indicate the following: a) the flow electrons in step 1 and in step 2 and b) draw the product D(product 2) resulting from step 2. Include stereo chemistry in your answer.arrow_forwardDefine the E2 mechanism for the Preparation of Alkenes ?arrow_forward
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