Draw the neutral product (after deprotonation) that results when the resonance contributor on the left in Part 2 reacts with methanol. draw structure ... + HBr
Basics in Organic Reactions Mechanisms
In organic chemistry, the mechanism of an organic reaction is defined as a complete step-by-step explanation of how a reaction of organic compounds happens. A completely detailed mechanism would relate the first structure of the reactants with the last structure of the products and would represent changes in structure and energy all through the reaction step.
Heterolytic Bond Breaking
Heterolytic bond breaking is also known as heterolysis or heterolytic fission or ionic fission. It is defined as breaking of a covalent bond between two different atoms in which one atom gains both of the shared pair of electrons. The atom that gains both electrons is more electronegative than the other atom in covalent bond. The energy needed for heterolytic fission is called as heterolytic bond dissociation energy.
Polar Aprotic Solvent
Solvents that are chemically polar in nature and are not capable of hydrogen bonding (implying that a hydrogen atom directly linked with an electronegative atom is not found) are referred to as polar aprotic solvents. Some commonly used polar aprotic solvents are acetone, DMF, acetonitrile, DMSO, etc.
Oxygen Nucleophiles
Oxygen being an electron rich species with a lone pair electron, can act as a good nucleophile. Typically, oxygen nucleophiles can be found in these compounds- water, hydroxides and alcohols.
Carbon Nucleophiles
We are aware that carbon belongs to group IV and hence does not possess any lone pair of electrons. Implying that neutral carbon is not a nucleophile then how is carbon going to be nucleophilic? The answer to this is that when a carbon atom is attached to a metal (can be seen in the case of organometallic compounds), the metal atom develops a partial positive charge and carbon develops a partial negative charge, hence making carbon nucleophilic.
#23 I just need help with the last part for the second screenshot
![Be sure to answer all parts.
Determine a stepwise mechanism for the following reaction that illustrates why two substitution
products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH)
under SN1 reaction conditions, even though it is a 1° alkyl halide.
1-bromohex-2-ene
Part 1:
Br
Part 2:
CH₂OH
The first step in the reaction proceeds according to which mechanism?
CH3CH₂CH₂CH=CHCH₂ + CH3OH
CH₂CH₂CH₂CH=CHCH₂2
Part 3 out of 5
Draw the missing resonance contributor.
Br
CH3CH₂CH₂CH=CH-CH₂ + Br
CH3CH₂CH₂CH=CHCH₂
H
Br
CH₂CH₂CH₂CH=C -CH₂ + CH₂OH
CH₂CH₂CH₂CH C
H
OCH 3
-CH₂ + CH₂OH
OCH ₁
H₂CH₂CH₂CH=CH₂
view structure
For the resonance contributor on the left in Part 2, choose the correct continuation of the mechanism.
O
+
+ Br
HBr](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb0d45dce-c646-4e67-b264-22576bb4d853%2F405b95a5-8160-4435-b0f6-2b4aface528e%2Fz79hdk9_processed.png&w=3840&q=75)
![Draw the neutral product (after deprotonation) that results when the resonance contributor on the left in
Part 2 reacts with methanol.
draw structure ...
+ HBr](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fb0d45dce-c646-4e67-b264-22576bb4d853%2F405b95a5-8160-4435-b0f6-2b4aface528e%2Fcnss8s_processed.png&w=3840&q=75)
![](/static/compass_v2/shared-icons/check-mark.png)
Trending now
This is a popular solution!
Step by step
Solved in 3 steps with 2 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)