
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Show stepwise mechanism by pushing arrows (fishhook) and drawing ALL intermediates. Draw a detailed mechanism for the addition of HBr to 3,3-dimethyl-1-butene in the presence of dimethlyperoxide. Show and label all steps including, initiation, propagation, and termination.

Transcribed Image Text:### Electrophilic Addition Reaction of Alkenes: Reaction with HBr
In this diagram, we observe the electrophilic addition reaction of an alkene with a hydrogen bromide (HBr) molecule.
#### Reactants:
1. **Alkene**: The structure of the reactant alkene is depicted on the left side of the image. It includes:
- A double bond between two carbon atoms (indicated by the double line).
- Two additional single bonds extending from the central carbon atoms forming a branched structure with a methyl group.
2. **Hydrogen Bromide (HBr)**: Denoted by the chemical symbol "HBr" above the arrow.
#### Reaction Description:
- The arrow indicates the direction of the chemical reaction, moving from the alkene (left) to the product (right).
- The presence of HBr signifies that the alkene undergoes an electrophilic addition reaction where HBr adds across the carbon-carbon double bond of the alkene.
#### Products:
The resulting product structure is depicted on the right side of the image, displaying:
- The original carbon chain modified through the addition reaction.
- The double bond in the alkene is broken, resulting in single bonds.
- A bromine (Br) atom is added to one of the carbon atoms that were previously part of the double bond.
- The hydrogen (H) atom from HBr is added to the other carbon atom from the double bond.
### Explanation of the Electrophilic Addition Reaction
In an electrophilic addition reaction, the pi electrons of the alkene double bond react with the electrophile (HBr in this case). The double bond breaks, and the electrophile is added to the resulting single-bonded carbon atoms. This type of reaction typically proceeds via a two-step mechanism involving the formation of a carbocation intermediate.
### Visualization of the Reaction Process:
1. **Initial Alkene Structure**: A branched alkene with a double bond.
2. **Interaction with HBr**: The double bond interacts with the HBr molecule.
3. **Product Formation**: The double bond is converted into two single bonds, with H and Br atoms added to the newly single-bonded carbons.
Understanding such reactions is pivotal in organic chemistry, as they form the foundation for synthesizing a wide array of organic compounds.
Expert Solution

This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
This is a popular solution
Trending nowThis is a popular solution!
Step by stepSolved in 2 steps with 1 images

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
- In the presence of acid such as H2SO4, 3,4-dimethyl-1-pentene undergoes isomerization to 2,3-dimethyl-2-pentene (shown below). Write a complete mechanism, showing all steps and using curved arrows to explain this observation.arrow_forwardPlease provide the major product of the following reaction via an E2 mechanism. ... Br KO Bu (one equivalent) t-BuOHarrow_forward(b) Show the mechanism of this reaction using proper arrow push notation. You must show all intermediates, formal charges, and necessary arrows. CH3 CH3 CH3 H20 H2SO4arrow_forward
- Write a plausible mechanism for this transformation. Only two sequential pericyclic reactions are required.arrow_forwardDraw the complete mechanism for the Grignard reaction of acetone (CH3)2C=O with PhMgBr followed by treatment with water. Be sure to show all starting materials, products, intermediates, and the required curved arrows to show the movement of electrons.arrow_forward1) a) Propose a detailed mechanism for the reaction of 2-bromo-2,3-dimethylbutane with sodium methoxide (NaOCH3), showing formation of the major product. Please include: 1) a perspective diagram of the substrate 2) a Newman projection 3) a perspective diagram illustration of the transition state 4) curved arrows, lone pairs, formal/partial charges etc. as appropriate Special Request: Please don't do anything with the spectator ion. b) Draw a simple ('flat,' no dashes/wedges required) Lewis diagram of the minor product. 1) Why is it minor? 2) How would you alter the reaction conditions given to favor the minor product?arrow_forward
- 1. Take a close look at the following reactions. (a) Draw the product in the box below. (b) Provide the mechanism in the space below the reaction scheme. H₂O, H₂SO4arrow_forwardProvide the complete mechanism using Curved Arrow Formalism for the reaction of 1-chloro-1-methylcyclopentane treated with NaOMe in MeOH. If more than one product is formed, which is the major, minor, and very minor product? Is the reaction SN1, SN2, E1, or E2. I appreciate the help on this question.arrow_forwardSelect the major product from the reaction sequence shown. 1) MezNH, [TSOH], - H2O 2) 3) HO مال منه NMez .OH ? ka taarrow_forward
- Please provide a detailed mechanism for the following transformation. Also, show the appropriate curved arrows to rationalize the next step. The quality of the electron pushing counts.arrow_forwardProvide mechanism and major organic product. 1) N2OCH,CH, CH,CH-OH 2) H,0 d.arrow_forward1. (a) Propose structure of the major product when A is reacted with dil. H2SO4. (b) Propose a mechanism for the reaction. Show all intermediate structures and all electron flow with arrows. OH dil. H2SO4arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY

Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning

Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education

Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education

Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning

Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY