Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 5, Problem 46DSP
Interpretation Introduction
Interpretation:
The role of ethanol in the given reaction is to be identified.
Concept introduction:
A catalyst is a species which itself remains unaltered in the reaction. It only reduces the activation energy and
A reactive intermediate is a species which is produced in one elementary step and consumed in in the other step. It is neither a reactant nor a product in the overall reaction.
Bronsted acids are species which have the capacity to donate a proton.
Bronsted bases are species which have the capacity to accept a proton.
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2. a. Write the complete reaction equation along with all the products that might be formed if 1-bromo-1-methylcyclohexane has an elimination reaction.b. Give the name of all the productsc. Which one is the major products? Give the explaination for your answer by writing the mechanism.
a. Write the complete mechanism, step by step, for the reaction shown in the image A, in such a way that it explains the formation of the products (Please do not forget the correct use of arrows!).
b. Write the complete mechanism (suppose an E2), step by step of the reaction shown in the figure B, in such a way that it explains the formation of a single product (DO NOT FORGET THE CORRECT USE OF THE ARROWS!). Using structures, justify the formation of the chosen product and not others.
c. Write the complete mechanism (suppose a bimolecular reaction), step by step of the reaction shown in the figure C, in such a way that it explains the formation of all possible products (there are three). (DON'T FORGET TO USE THE ARROWS CORRECTLY!). Watch out for stereochemistry!
Write the appropriate reaction mechanism for the formation of the most stable alkene that will occur as a result of the reactions given below.
Chapter 5 Solutions
Organic Chemistry - Standalone book
Ch. 5.1 - Prob. 1PCh. 5.1 - Prob. 2PCh. 5.1 - Many compounds contain more than one functional...Ch. 5.2 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.4 - Classify the isomeric C4H10O alcohols as being...Ch. 5.5 - Bromine is less electronegative than chlorine, yet...Ch. 5.6 - Prob. 8PCh. 5.7 - Prob. 9PCh. 5.8 - Prob. 10P
Ch. 5.8 - Prob. 11PCh. 5.9 - Carbocations are key intermediates in petroleum...Ch. 5.9 - Prob. 13PCh. 5.9 - Prob. 14PCh. 5.11 - Prob. 15PCh. 5.13 - Prob. 16PCh. 5.14 - For the reaction of a primary alcohol RCH2OH with...Ch. 5.15 - Prob. 18PCh. 5 - Write structural formulas for each of the...Ch. 5 - Prob. 20PCh. 5 - Prob. 21PCh. 5 - Write structural formulas for all the...Ch. 5 - Prob. 23PCh. 5 - Prob. 24PCh. 5 - Epichlorohydrin is the common name of an...Ch. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Prob. 28PCh. 5 - Some of the most important organic compounds in...Ch. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - The reaction of 2,2-dimethyl-1-propanol...Ch. 5 - (a) Assuming that the rate-determining elementary...Ch. 5 - The reaction of 3-tert-butyl-3-pentanol with...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46DSPCh. 5 - Prob. 47DSPCh. 5 - Prob. 48DSPCh. 5 - Prob. 49DSPCh. 5 - Prob. 50DSPCh. 5 - Prob. 51DSPCh. 5 - Prob. 52DSP
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- Illustrate the reaction mechanism for the ethylation of p-cyclopropyllphenol (other reactants: AlCl3 and ethylchloride). Refer to Friedel-Craft Alkylation mechanism as your guide in doing this mechanism. Show ALL partial charges in the EACH structure using BLUE color. Arrows should be written using RED color.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_forwardAnswer the following question below for the reaction of (R)-1-bromo-1-phenylethane with sodium azide in a water/ethanol solution. a) Kinetics experiments have determined that the reaction is only dependent on the concentration of 1-bromo-1-phenylethane. Is this an SN1 or SN2 mechanism? b) Draw an energy diagram for the reaction. Label all parts. Assume that the products are lower in energy than the reactants. c) Show the mechanism of the reaction, including stereochemistry, using good curved arrow notation, to clearly illustrate the product(s) obtained from this reaction. Label the product(s) with absolute configuration where needed. d) Is the solution optically active after the reaction has taken place? Explain.arrow_forward
- Read these directions carefully. For the reaction of 3-methyl-1-propene with Cl2 and H2O shown below, fill in the details of the mechanism. Draw the appropriate chemical structures and use an arrow to show how pairs of electrons are moved to make and break bonds during the reaction. Be sure to write all lone pairs of electrons and all formal charges. Finally, in the boxes provided by the arrows, write which kind of mechanistic element is being indicated, such as "make a bond", "add a proton", etc.arrow_forwardImagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) In analyzing the products, you discover that the substitution pattern resulting from the reaction with phenol differs from the reaction with nitrobenzene. Explain this difference in substitution patterns using one or more judiciously selected reaction mechanisms or portions of mechanisms.arrow_forwardSecondary alcohols are often dehydrated in an E2 reaction to give an alkene. Elimination follows Zaitsev's rule to give the more substituted alkene as the major product. Since the reaction occurs via an E2 mechanism, there is no risk of rearrangement of the carbon skeleton as could possibly occur if the elimination occurred via an E1 mechanism with a carbocation intermediate.Draw curved arrows to show the movement of electrons in this step of the mechanism.arrow_forward
- The following flow chart connects three of the reactions we have discussed that involve carbocation intermediates. Each arrow may represent more than one elementary step in a mechanism.Arrows 1 and 2 summarize the conversion of alcohols to alkyl halides, 3 and 4 the dehydrohalogenation of an alkyl halide to an alkene by the E1 mechanism, and 1 and 4 the formation of an alkene by dehydration of an alcohol. The reaction indicated by arrow 5 constitutes a major focus of the next chapter. There we will explore reactions that give overall addition to the double bond by way of carbocation intermediates. One such process converts alkenes to alkyl halides (5 + 2), another converts alkenes to alcohols (5 + 6).What term best describes the relationship between an alkene and a carbocation? A. Isomers B. Resonance contributors C. Alkene is conjugate acid of carbocation D. Alkene is conjugate base of carbocationarrow_forward] The reaction of 2-bromopropane and sodium ethoxide in ethanol reacts 6.7 times faster than 2-bromo-1-deuteriopropane under the same conditions. Explain what mechanism this data is consistent with, and whyarrow_forwardThe following elimination reaction results in a mixture of products. Explain why the major products obtained in larger quantities than the minor products. Use chemical structures as necessary to justify your answer.arrow_forward
- for each of the following reactions. Give all the steps of the mechanism and use curved arrows to clearly indicate how the reaction is occuring. a. write the complete SN1 mechanism for the methanolysis (i.e. reaction with CH3OH) of the 2-chloro-2-methylpropane b. write the complete SN2 mechanism for the reaction of (R)-2-butanal with HBr c. Wrtie the complete E2 mechanism for the reaction of 2-bromo-2-methylbutane with CH3-/CH3OH.arrow_forwardGive a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with sodium methoxide. Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Discuss the stability of the final compoundarrow_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_forward
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