I have the SN2! I need the
SN1!Homework Answers
General guidance
The concept used to solve this problem is and . The substrate is a secondary alkyl halide and the nucleophile is a strong base.
In reactions, rearrangement of carbocation takes place. Here, racemic mixture of products will be formed.
In , the attack of nucleophile takes place from the back side, so inversion of configuration takes place in the product.
reaction is a two-step reaction. The rate of the reaction depends only on the concentration of substrate. It does not depend on the concentration of incoming nucleophile.
reaction is a single step reaction. The rate of the reaction depends on both concentration of substrate and concentration of nucleophile.
Step-by-step
Step 1 of 2
(a)
The reaction is as follows:
Here, the formed product is 2-methylpentan-2-ol.
The major product of the reaction proceeds by [{{ m{S}}_{ m{N}}}1]mechanism is as follows:
Explanation | Hint for next step
Treatment of 3-bromo-2-methylpentane with hydroxide ion gives 2-methyl-2-pentanol. Here, the secondary carbocation is formed by the heterolytic cleavage of C-Br bond. Next, by the 1,2-hydride shift, the secondary carbocation is converted to more stable tertiary carbocation. Now, the hydroxide ion attacks the tertiary carbocation and forms the corresponding product.
Step 2 of 2
(b)
The reaction is as follows:
Here, the formed product is 2-methylpentan-3-ol.
The major product of the reaction proceeds by [{{ m{S}}_{ m{N}}}{ m{2}}]mechanism is as follows:
Explanation
Treatment of 3-bromo-2-methylpentane with the hydroxide ion gives 2-methylpentan-3-ol. This reaction proceeds through mechanism. Here, the nucleophile attacks from the back the side of the carbon bearing the leaving group, so, the bromide ion expels out and forms the required product.
Answer
The major product of the reaction proceeds by [{{ m{S}}_{ m{N}}}1]mechanism is as follows:
The major product of the reaction proceeds by [{{ m{S}}_{ m{N}}}{ m{2}}]mechanism is as follows:
Answer only
The major product of the reaction proceeds by [{{ m{S}}_{ m{N}}}1]mechanism is as follows:
The major product of the reaction proceeds by [{{ m{S}}_{ m{N}}}{ m{2}}]mechanism is as follows:
Add Answer to:
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State whether the following reaction is Sn2, Sn1 or E2
mechanism and draw the structure of the major organic product(s).
If Sn1, consider rearranged products too.
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Draw
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reaction problem Draw the major, neutral organic product(s) for each reaction below.
reaction problem
Draw the major, neutral organic product(s) for each reaction below.
Draw the major, neutral organic product obtained if: the reaction proceeds by the SN1 mechanism the reaction proceeds by the SN2 mechanism. Draw the major, neutral organic product for each substitution reaction below. (For this question, assume that each substitution reaction goes to completion. Disregard elimination.)
Draw the major, neutral organic product obtained if: the reaction proceeds by the SN1 mechanism the reaction proceeds by the SN2 mechanism. Draw the major, neutral organic product for each substitution reaction below. (For...
Draw the major, neutral organic product obtained if: the reaction proceeds by the Sn1 mechanism the reaction proceeds by the Sn2 mechanism.
State whether the following reaction is Sn2, Sn1 or E2
mechanism and draw the structure of the major organic product(s).
If Sn1, consider rearranged products too.
ОРОЗН ОН
Draw the structure(s) of the major neutral organic product(s) obtained after workup of the following reaction. HNO, acetic anhydride 20° two isomers CH3 • You do not have to consider stereochemistry. • If no reaction occurs, draw the organic starting material. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu.
(a) For each substitution reaction, circle whether it proceeds by an Sy1 or S 2 mechanism. (1.5 pts) (b) Draw the major organic product for each reaction. Be sure to indicate the appropriate stereochemistry, where necessary (1.5 pts) 2. NaCN S1 or S 2? Br THF SN1 or Sy2? но CH3 Hас, SN1 or SN2? CH,он
Draw the structure(s) of the major organic product(s) of the
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obtained after workup of the following reaction:
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