What would be the major product of the following reaction sequence? 1. Br₂, hv □ 2. t-BuOK, t-BuOH, heat I ỢCode III OI III OII OV ON II Ot-Bu OH IV Ot-Bu
Reactive Intermediates
In chemistry, reactive intermediates are termed as short-lived, highly reactive atoms with high energy. They rapidly transform into stable particles during a chemical reaction. In specific cases, by means of matrix isolation and at low-temperature reactive intermediates can be isolated.
Hydride Shift
A hydride shift is a rearrangement of a hydrogen atom in a carbocation that occurs to make the molecule more stable. In organic chemistry, rearrangement of the carbocation is very easily seen. This rearrangement can be because of the movement of a carbocation to attain stability in the compound. Such structural reorganization movement is called a shift within molecules. After the shifting of carbocation over the different carbon then they form structural isomers of the previous existing molecule.
Vinylic Carbocation
A carbocation where the positive charge is on the alkene carbon is known as the vinyl carbocation or vinyl cation. The empirical formula for vinyl cation is C2H3+. In the vinyl carbocation, the positive charge is on the carbon atom with the double bond therefore it is sp hybridized. It is known to be a part of various reactions, for example, electrophilic addition of alkynes and solvolysis as well. It plays the role of a reactive intermediate in these reactions.
Cycloheptatrienyl Cation
It is an aromatic carbocation having a general formula, [C7 H7]+. It is also known as the aromatic tropylium ion. Its name is derived from the molecule tropine, which is a seven membered carbon atom ring. Cycloheptatriene or tropylidene was first synthesized from tropine.
Stability of Vinyl Carbocation
Carbocations are positively charged carbon atoms. It is also known as a carbonium ion.
![The question asks for the major product of a given reaction sequence involving two steps. Below is a detailed transcription and explanation suitable for an educational context.
**Question:**
What would be the major product of the following reaction sequence?
**Reaction Sequence:**
1. Reaction with \( \text{Br}_2 \), initiated by \( h\nu \) (light).
2. Followed by treatment with \( \text{t-BuOK, t-BuOH,} \) and heat.
**Given Compounds:**
- The starting compound is a simple cyclohexane derivative with a single methyl group.
- Five possible products (I - V) are depicted:
- **I:** A cyclohexane with a methyl and a bromine substituent.
- **II:** A cyclohexane with a tert-butoxy group (\( \text{Ot-Bu} \)).
- **III:** A cyclohexene structure with a single substituent.
- **IV:** A cyclohexane with a hydroxyl group.
- **V:** A cyclohexane with an \( \text{Ot-Bu} \) substituent on a different position from II.
**Options for Major Product:**
- I
- III
- II
- V
- IV
Understanding the reaction sequence requires analyzing the mechanistic pathway:
1. **First Step:** The \( \text{Br}_2 / h\nu \) reaction suggests a radical halogenation process, likely introducing a bromine atom at the tertiary position of the methyl group.
2. **Second Step:** Treatment with \( \text{t-BuOK, t-BuOH,} \) and heat indicates an elimination or substitution process. This is typical for promoting the formation of an ether or possibly an elimination to form an alkene via E2 elimination.
The educational focus should be on:
- Radical halogenation under light (producing compound I).
- The nucleophilic substitution or elimination process converting the halide into an ether (compound II) or promoting an elimination to form an alkene (compound III).
To determine the exact major product, consider the likelihood of elimination vs. substitution under the treatment conditions.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F73b7e734-4d28-4aad-9c82-100ed88eb135%2Fca4f3ac6-952c-4bca-86ed-e5fbf8d34c31%2F6yzt1nzc_processed.jpeg&w=3840&q=75)
![](/static/compass_v2/shared-icons/check-mark.png)
Trending now
This is a popular solution!
Step by step
Solved in 2 steps with 1 images
![Blurred answer](/static/compass_v2/solution-images/blurred-answer.jpg)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
![Chemistry](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
![Principles of Instrumental Analysis](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
![Organic Chemistry](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
![Chemistry: Principles and Reactions](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
![Elementary Principles of Chemical Processes, Bind…](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)