Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 8.6, Problem 8P
Instead of the three-step process of Mechanism 8.3, the following two-step mechanism might be considered:
1.
2.
This mechanism cannot be correct! What is its fundamental flaw?
Mechanism 8.3
Acid-catalyzed Hydration of
The Overall Reaction
The Mechanism:
Step 1: Protonation of the carbon–carbon double bond in the direction that leads to the more stable carbocation:
Step 2: Water acts as a nucleophile to capture
Step 3: Deprotonation of
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
8. Consider the nucleophilic substitution reaction below:
CI:
+ CH3OH
step 1
intermediate A
CH3OH
step 2
H
CH3
Draw the mechanism by using the curved arrow notation on the above reaction, to indicate the
electron movement for both the formation of the intermediate A and for the product. You will
need to draw Intermediate A and include the side product (s). Please show electron pairs and
charges
Step 4a: Classify step.
The target product is present, but the reaction is not over. The ethoxide ion has been regenerated.
:0:
:0:
What is the key process in the next step of the mechanism?
proton transfer
formation of a o bond between nucleophile and electrophile
loss of a leaving group
carbocation rearrangement (e.g., methyl or hydride shift)
(dehydrobromination)
A chemist carried out an elimination reaction
of 1,1-dimethyl-2-
bromocyclopentane. The chemist expected the
reaction to yield alkene Z as product. However,
alkene Z DID NOT form. Instead, three alkenes
were produced: one alkene was the major
product, the other two alkenes was the minor
products.
What was the major alkene product that
formed?
Br
Select one:
A. I
B. II
C. IV
D. III
alcohol
HEAT
||
Z
=
+
(HBr)
IV
Chapter 8 Solutions
Organic Chemistry - Standalone book
Ch. 8.1 - What three alkenes yield 2-methylbutane on...Ch. 8.2 - Prob. 2PCh. 8.2 - Prob. 3PCh. 8.3 - Prob. 4PCh. 8.4 - Prob. 5PCh. 8.4 - Give a structural formula for the carbocation...Ch. 8.5 - Prob. 7PCh. 8.6 - Instead of the three-step process of Mechanism...Ch. 8.6 - The rates of hydration of the two alkenes shown...Ch. 8.6 - Is the electrophilic addition of hydrogen chloride...
Ch. 8.7 - You can calculate the equilibrium constant for the...Ch. 8.7 - Does the presence or absence of a catalyst such as...Ch. 8.7 - The gas phase reaction of ethanol with hydrogen...Ch. 8.8 - Prob. 14PCh. 8.8 - Hydroborationoxidation of -pinene, like its...Ch. 8.10 - Arrange the compounds 2-methyl-1-butene,...Ch. 8.10 - Give the structure of the product formed when each...Ch. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.12 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.13 - Prob. 22PCh. 8.14 - Prob. 23PCh. 8.14 - Prob. 24PCh. 8 - How many alkenes yield...Ch. 8 - Prob. 26PCh. 8 - Catalytic hydrogenation of...Ch. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - A single epoxide was isolated in 7984% yield in...Ch. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - On catalytic hydrogenation over a rhodium...Ch. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - 1-Butene has a higher heat of hydrogenation than...Ch. 8 - Match the following alkenes with the appropriate...Ch. 8 - The heats of reaction were measured for addition...Ch. 8 - Complete the following table by adding + and -...Ch. 8 - Match the heats of hydrogenation (107 kJ/mol,...Ch. 8 - The iodination of ethylene at 25 C is...Ch. 8 - Specify reagents suitable for converting...Ch. 8 - (a) Which primary alcohol of molecular formula...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Prob. 50PCh. 8 - On being heated with a solution of sodium ethoxide...Ch. 8 - Compound A (C7H15Br) is not a primary alkyl...Ch. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - A mixture of three alkenes (A, B, and C) was...Ch. 8 - Reaction of 3,3-dimethyl-1-butene with hydrogen...Ch. 8 - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol...Ch. 8 - Prob. 58PCh. 8 - East Indian sandalwood oil contains a hydrocarbon...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - On the basis of the mechanism of acid-catalyzed...Ch. 8 - As a method for the preparation of alkenes, a...Ch. 8 - Which of the following is the most reasonable...Ch. 8 - Prob. 68PCh. 8 - Oxymercuration Concerns about mercurys toxicity...Ch. 8 - Prob. 70DSPCh. 8 - Prob. 71DSPCh. 8 - Prob. 72DSPCh. 8 - Prob. 73DSPCh. 8 - Oxymercuration Concerns about mercurys toxicity...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider the reaction below to answer the following question(s): H Ph 7 H₂C Ph NTÖH ** A) Draw a Newman projection of the reactive conformation of the starting material. B) Write the product that results from the electron flow in the reaction, clearly indicating any stereochemistry. C) What is the name of this reaction mechanism? D) What is the rate law for this reaction?arrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. OH CH3 + + H3C CH₂ CH3 First stage in synthesis of the preservative BHT • You do not have consider stereochemistry. • Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one. ▼ H3PO4 ? OH CH3 CH3 CH3 CH3arrow_forwardConsider the two energy diagrams given below. B Reaction progress Reaction progress Which of the following is correct with respect to these diagrams? O A could represent an E2 reaction B could represent an E1 reaction A could represent an E1cb reaction O A could represent and E1 reaction B could represent an E1cb reaction Energyarrow_forward
- 5. Consider the following reaction: Br EtO Major Minor i. Draw the reaction mechanism for the formation of BOTH products. ii. Explain why the major product in this reaction is trans-isomer whereas cis- isomer is the minor product.arrow_forward16. Consider the free energy diagram below and select the answer that correctly completes the following statements. An example of a transition state is The overall free energy change of the reaction (AG°) is free energy A Reaction Coordinate C12H18 Cl2 H3C B H H The rate determining step for the reaction is C 17. A compound with the molecular formula below has no double or triple bonds. How many rings does it contain? CH 3 D 18. The correct IUPAC name for the following compound is Y E a. 0 rings b. 1 ring 2 rings 3 rings 4 rings a. B, A to C, Y b. C, C to E, X c. D, A to C, X d. C, C to E, Y e. B, A to E, Y C. d. e. a. 1,2 dimethylcyclohexane b. trans-1,2-dimethylcyclohexane c. cis-1,2-dimethylcyclohexane d. trans- 1,6-dimethylcyclohexane e. cis-1,6-dimethylcyclohexanearrow_forwardQ6: Consider the following reaction: (CH3) 3CBR + H20 (CH3) 3COH + HBr 1. a: What will happen to the rate of the reaction if [ (CH3) 3CBr] is doubled b: What will happen to the rate of the reaction if [H0] is doubled c: What will happen to the rate of the reaction if both [ (CH3) 3CB1] and [H20] are doubledarrow_forward
- An SN1 reaction is shown in the box; the reaction energy profile diagram for this reaction is shown below. Identify the location for Compound I on the reaction profile. A) 1 B) 2 C) 3 D) 4 E) 5arrow_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 H3PO4 HO, + H3C CH3 HO HO First stage in synthesis of the epoxy and polycarbonate ingredient bisphenol-A You do not have to consider stereochemistry. Include all valence lone pairs in your answer. In cases where there is more than one answer, just draw one.arrow_forwardConsider this reaction: Br CH;OH Br-Br H3CO The mechanism proceeds through a first cationic intermediate, intermediate 1. Nucleophilic attack leads to intermediate 2, which goes on to form the final product. In cases that involve a negatively charged nucleophile, the attack of the nucleophile leads directly to the product. Br + CH3OH Br Intermediate 1 Intermediate 2 (product) In a similar fashion, draw intermediate 1 and intermediate 2 (final product) for the following reaction. OH + Br2 + HBr Br racemic mixturearrow_forward
- Vhich of the following statements is incorrect? * 3 p Hammond-Leffler Postulate states that there is a strong resemblance between the transition state and the product in an endothermic reaction. Hammond-Leffler Postulate states that there is a strong resemblance between the transition state and the reactants in an exothermic reaction. The presence of more electron-donating alkyl groups ineffectively delocalize the positive charge in an organic molecule, making it less stable. The dehydration of primary alcohol proceeds via E2 mechanism. All of the abovęarrow_forwardQuestion 1 of 20 Show the mechanism for the reaction conducted at -5 "C in CCI, cyclohexene + bromine dibromocyclohexane Draw structures, including charges and electrons, and add curved arrows. Details count. Step I Add three curved arrows to the first step. Draw the step 1 products: I organic species and I inorganic species. Select Draw Rings More Erase Select Draw Rings More Erase Br Brarrow_forward1. 2-Chloro-2-methylpropene reacts with water in three steps to yield 2-methyl-2-propanol. The first step is slower than the second, which in turn is much slower that the third. The reaction takes place slowly at room temperature, and the equilibrium constant is approximately 1. Which of the energy diagrams for the reaction are drawn and labeled correctly. Make sure the energy levels are consistent with the information given.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY