Homework Answers
6.6
After E2 reaction there is no electrophile in the solution as reaction medium is basic, electrophile is needed to reverse the reaction, because alkene always first react with an electrophile then nucleophile attack on it.
Hence, reverse of E2 is not possible.
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5) This El reaction is reversible. Explain how the reaction reverses using an electron-pushing! mechanism with...
The E1 reaction is reversible. Explain how the reaction reverses using an electron-pushing mechanism with bother...
The E1 reaction is reversible. Explain how the reaction reverses using an electron-pushing mechanism with bother alkene products. Furthermore, the E2 reaction is irreversible, explain why (7pts)
how does the mixture of isomeric alkenes produced by an acid-catalyzed dehydration reaction compare with the...
how does the mixture of isomeric alkenes produced by an
acid-catalyzed dehydration reaction compare with the alkene mixture
from a base-catalyzed dehydrochlorination reaction? Are either or
both sets or products influenced primarily by product
stability?
E1/E2 Elimination Reactions. Acid-Catalyzed Dehydration of 2-Me Base-Catalyzed Dehydrochlorination of 2-Chloro-2-methylbutane Acid-Catalyzed Dehydration of 2-Methyl-2-butanol and Adapted for an experiment published in More J.R - Hammond, C.N. Schatz, PF: Morrill, T.C.: Modern Projects and P. Hammond CN: Schatz, P.F., Morrill... Experiments in Organic Chemistry, 2nd...
5. Explain how the following changes will influence the rate of the reaction of 2-bromo-2- methylbutane...
5. Explain how the following changes will influence the rate of the reaction of 2-bromo-2- methylbutane with methanol: a. The alkyl halide is changed to 2-chloro-2-methylbutane b. The alkyl halide is changed to 2-chloro-3-methylbutane 6. What product(s) do you predict for the following reactions? Be specific with regard to stereochemistry. Also, indicate which stereoisomer will be more predominant. a. R-2-bromopentane + CH30 b. R-3-bromo-3-metylheptane + CH3OH C. 1-bromo-2-butene + CH30 d. 1-bromo-2-butene + CH3OH e. E2 reaction of 2-bromobutane f....
Complete the electron-pushing mechanism for the E1 reaction when 2-methylbutan-2-ol is treated with 20% sulfuric acid....
Complete the electron-pushing mechanism for the E1 reaction when
2-methylbutan-2-ol is treated with 20% sulfuric acid.
Hint: The E1 mechanism involves dissociation of the hydroxyl
group from the substrate. The acid is used to convert the hydroxyl
group to a good leaving group. Do not delete any pre-drawn
bonds/charges/lone pairs.
Complete the electron-pushing mechanism for the E1 reaction when 2-methylbutan-2-ol is treated with 20% sulfuric acid Map a) Use two curved arrows to show the fast b) Use a curved...
Consider the synthesis of tert-amyl chloride (2-chloro-2-methylbutane) from 2-methyl-2-butanol and HCl which has SN1 reaction. Explain...
Consider the synthesis of tert-amyl chloride (2-chloro-2-methylbutane) from 2-methyl-2-butanol and HCl which has SN1 reaction. Explain if a SN1 reaction would occur if the following(below) was changed. If an SN1 does occur, then state the IUPAC name of the product formed and compare the rate of reaction to the rate of the original reaction . In the event that SN1 does not occur, state the type of reaction that may occur and draw all the major products that could be...
d. AG-AH-AS/T 42. How many stereoisomers of 4-chloro-2-methylpentane (CHs):CHCH:CHCICHs, exist? a. I b. 2 c. 3...
d. AG-AH-AS/T 42. How many stereoisomers of 4-chloro-2-methylpentane (CHs):CHCH:CHCICHs, exist? a. I b. 2 c. 3 d. 4 43. What is the major organic product obtained from the reaction of 1-butanol with aqueous HBr at reflux? a. 1-bromobutane b. 2-bromobutane c. 2-bromo-1-butanol d. 1-butene 44. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide? a. methanol b. ethanol 2-propanol d. 2-methyl-2-propanol C. 45.Which of the following alcohols undergoes the most H2SO4 to give rapid...
Dehydration Experiment: 1. Show all appropriate electron-pushing arrows to explain the formation of each of the...
Dehydration Experiment: 1. Show all appropriate electron-pushing arrows to explain the formation of each of the observed products in the following reaction. Because intermediates have been provided for you, all arrows must be perfect and must be clear to get credit. 9M H,SO 20- s-d-o g- 2. "Rearrangements" like you see above are fairly common in Snl (and El) reactions, but are never seen in Sy2 or E2 reactions. Why don't those latter mechanisms ever allow rearrangement to occur?
What is Zaitsev’s rule? Give the mechanism for the acid-catalyzed E1 reaction of 2-butanol. Give the...
What is Zaitsev’s rule? Give the mechanism for the acid-catalyzed E1 reaction of 2-butanol. Give the mechanism for the base-catalyzed E2 reaction of 2-bromobutane. Draw all possible products. You expect three products from the elimination reaction 2-butanol. What are they? The E2 mechanism is a one-step mechanism. True or False? Explain. Which of these two alcohols would you expect to be more reactive under H3PO4/aqueous conditions? Why? Give the structure of the main product in both cases. 1-phenyl-1-propanol 1 -cyclohexyl-1-propanol...
how does the mixture of isomeric alkenes produced by an
acid-catalyzed dehydration reaction compare with the alkene mixture
from a base-catalyzed dehydrochlorination reaction? Are either or
both sets or products influenced primarily by product
stability?
E1/E2 Elimination Reactions. Acid-Catalyzed Dehydration of 2-Me Base-Catalyzed Dehydrochlorination of 2-Chloro-2-methylbutane Acid-Catalyzed Dehydration of 2-Methyl-2-butanol and Adapted for an experiment published in More J.R - Hammond, C.N. Schatz, PF: Morrill, T.C.: Modern Projects and P. Hammond CN: Schatz, P.F., Morrill... Experiments in Organic Chemistry, 2nd...
5. Explain how the following changes will influence the rate of the reaction of 2-bromo-2- methylbutane with methanol: a. The alkyl halide is changed to 2-chloro-2-methylbutane b. The alkyl halide is changed to 2-chloro-3-methylbutane 6. What product(s) do you predict for the following reactions? Be specific with regard to stereochemistry. Also, indicate which stereoisomer will be more predominant. a. R-2-bromopentane + CH30 b. R-3-bromo-3-metylheptane + CH3OH C. 1-bromo-2-butene + CH30 d. 1-bromo-2-butene + CH3OH e. E2 reaction of 2-bromobutane f....
Complete the electron-pushing mechanism for the E1 reaction when
2-methylbutan-2-ol is treated with 20% sulfuric acid.
Hint: The E1 mechanism involves dissociation of the hydroxyl
group from the substrate. The acid is used to convert the hydroxyl
group to a good leaving group. Do not delete any pre-drawn
bonds/charges/lone pairs.
Complete the electron-pushing mechanism for the E1 reaction when 2-methylbutan-2-ol is treated with 20% sulfuric acid Map a) Use two curved arrows to show the fast b) Use a curved...
d. AG-AH-AS/T 42. How many stereoisomers of 4-chloro-2-methylpentane (CHs):CHCH:CHCICHs, exist? a. I b. 2 c. 3 d. 4 43. What is the major organic product obtained from the reaction of 1-butanol with aqueous HBr at reflux? a. 1-bromobutane b. 2-bromobutane c. 2-bromo-1-butanol d. 1-butene 44. Which of the following alcohols reacts fastest with HBr to give the corresponding alkyl bromide? a. methanol b. ethanol 2-propanol d. 2-methyl-2-propanol C. 45.Which of the following alcohols undergoes the most H2SO4 to give rapid...
Dehydration Experiment: 1. Show all appropriate electron-pushing arrows to explain the formation of each of the observed products in the following reaction. Because intermediates have been provided for you, all arrows must be perfect and must be clear to get credit. 9M H,SO 20- s-d-o g- 2. "Rearrangements" like you see above are fairly common in Snl (and El) reactions, but are never seen in Sy2 or E2 reactions. Why don't those latter mechanisms ever allow rearrangement to occur?
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