Predict the major alkene product of the following E1 reaction: (EQUATION CAN'T COPY)

Name: Problem 38, Chapter 11: Organic Chemistry
Uploaded: 2020-06-18T04:20:50-08:00
Duration: 3 min 32 s
Channel: Travis Maslanik
Description: Predict the major alkene product of the following E1 reaction: (EQUATION CAN'T COPY)

step 1 So we are given the following reaction. We have an organic compound that is being reacted with a

Predict the major alkene product of the following E1...

Key Concepts

Elimination Reactions

Elimination reactions are a class of organic reactions where elements are removed from a molecule, resulting in the formation of a double bond. They play a crucial role in creating unsaturated structures, such as alkenes, and typically follow either an E1 or E2 mechanism.

E1 Reaction Mechanism

The E1 mechanism is a two-step elimination process where the first step involves the formation of a carbocation intermediate after the leaving group departs. In the second step, a base removes a proton from an adjacent carbon atom leading to the formation of a double bond. The unimolecular rate-determining step depends solely on the concentration of the substrate.

Carbocation Stability

Carbocation stability is a key factor in E1 reactions; more substituted carbocations are generally more stable due to hyperconjugation and inductive effects. This stability can influence which carbocation intermediate forms and subsequently determine the major alkene product by favoring pathways that lead to the most substituted, and often more stable, alkene.

Zaitsev's Rule

Zaitsev's rule predicts that in elimination reactions, the more substituted alkene—the one with the greater number of alkyl substituents on the double bond—will generally be the major product. This is because such alkenes are thermodynamically more stable due to enhanced hyperconjugation and electron donation from the alkyl groups.

Transcript

00:01 So we are given the following reaction.

00:03 We have an organic compound that is being reacted with acetic acid and heat.

00:08 We're also given that this occurs with an e1 elimination reaction.

00:12 So we want to go ahead and predict what products we're going to get from this reaction.

00:16 And of course the first step we know for any e1 elimination reaction is that our leaving group is first going to leave.

00:24 So that would be our bromide alkali.

00:27 So that will leave.

00:30 And we're going to get the formation of a.

00:31 A carbocadion.

00:33 Here in our case it's going to be a tertiary carbocation.

00:37 And now we can go ahead and do our deprotonation with our acetic acid.

00:42 Cetic acid is a pretty weak base, but once we put a lot of heat into it, it's capable of deprotinating.

00:48 So let's say we're going to deprotonate this hydrogen here.

00:54 And so we have our acetic acid, great, which is going to come in now, deprotonate that, and the electrons of this hydrogen are going to get pushed.

01:05 Down here.

01:07 So that is going to give us the following product where we get this formation of this salcine.

01:17 Now we can also deprotonate at a different hydrogen as well.

01:23 So let's say since we have our carbocetion intermediate here, let's say we make that red here, deprotonate at this beta hydrogen...

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