New User Special Price Expires in

Let's log you in.

Sign in with Facebook


Don't have a StudySoup account? Create one here!


Create a StudySoup account

Be part of our community, it's free to join!

Sign up with Facebook


Create your account
By creating an account you agree to StudySoup's terms and conditions and privacy policy

Already have a StudySoup account? Login here

Sn1, Sn2, E1, E2 mechanism crash course

by: Rachel Taylor

Sn1, Sn2, E1, E2 mechanism crash course Chem 372

Marketplace > Eastern Michigan University > Chemistry > Chem 372 > Sn1 Sn2 E1 E2 mechanism crash course
Rachel Taylor
GPA 3.5

Preview These Notes for FREE

Get a free preview of these Notes, just enter your email below.

Unlock Preview
Unlock Preview

Preview these materials now for free

Why put in your email? Get access to more of this material and other relevant free materials for your school

View Preview

About this Document

This covers the substitution and elimination mechanisms. It includes a table condensing properties of each mechanism into the most important information.
Organic Chemistry
Dr. Friebe
Class Notes
Organic Chemistry, Chemistry
25 ?




Popular in Organic Chemistry

Popular in Chemistry

This 2 page Class Notes was uploaded by Rachel Taylor on Tuesday January 19, 2016. The Class Notes belongs to Chem 372 at Eastern Michigan University taught by Dr. Friebe in Winter 2016. Since its upload, it has received 25 views. For similar materials see Organic Chemistry in Chemistry at Eastern Michigan University.


Reviews for Sn1, Sn2, E1, E2 mechanism crash course


Report this Material


What is Karma?


Karma is the currency of StudySoup.

You can buy or earn more Karma at anytime and redeem it for class notes, study guides, flashcards, and more!

Date Created: 01/19/16
Sn1 and Sn2 Mechanisms Sn2 Sn1 E2 E1 Number of R 1˚ 3˚ 3˚ 3˚ groups favored Rate equation R=k[R-X][Nu] R=k[R-X] R=k[R-X][B] R=k[R-X] Stereochemistry Inversion Mix Antiperiplanar mix Solvent Aprotic Polar Protic Polar Aprotic Polar Protic Nucleophile Strong Weak Strong Weak Best leaving group Iodine Iodine Iodine Iodine Number of Steps 1 2 1 2 Table 1: Overview of Sn1, Sn2, E1, and E2 mechanisms. Number of R groups favored: With Sn1, E1, and E2, the increase of R groups stabilize the carbocation intermediates due to the ability to distribute charge. With Sn2 reactions, since. E2 and Sn2 are very similar, except that Sn2 reactions have steric hindrance with the increase of R groups. When the Nucleophile attacks the molecule, it does not want to be close to other atoms except the carbon where the substitution is taking place (figure 1). Figure 1: Sn2 Nucleophilic substitution. Leaving group: Iodine is always the best leaving group because it is the biggest halogen. The larger the halogen, the better it is at stabilizing a negative charge. Rate Equations: The rate equations of Sn2 and E2 are straight forward: as the concentration of either compound, the rate increases. In Sn1 and E1 reactions, they are two step mechanisms. Because of this, their rate depends on the slowest step in the reaction. This slow step is when the halogen leaves creating a highly unstable carbocation. Thus, the rate equation for both E1 and Sn1 depends on the concentration of the electrophile, not the Base/Nucleophile. Stereochemistry: The most important thing to know about stereochemistry is Sn1 and E1 reactions make mixtures of stereoisomers, and Sn2 mechanisms invert the stereochemistry. Solvent: In Sn1 and E1 mechanisms, polar protic solvents are favored because they hydrogen bond with the leaving group, and it has dipole-dipole interactions with the carbocation, stabilizing the charges. In E2 and Sn2 mechanisms, the anion needs to attack the alkyl halide, so if the charge was stabilized in a polar protic solvent, it would slow down the reaction. Nucleophile: Sn2 and E2 need strong nucleophiles in order to attack the alkyl halide forcing the leaving group to leave. In Sn1 and E1 mechanisms, weak nucleophiles are used to avoid competing Sn2 and E2 mechanisms.


Buy Material

Are you sure you want to buy this material for

25 Karma

Buy Material

BOOM! Enjoy Your Free Notes!

We've added these Notes to your profile, click here to view them now.


You're already Subscribed!

Looks like you've already subscribed to StudySoup, you won't need to purchase another subscription to get this material. To access this material simply click 'View Full Document'

Why people love StudySoup

Steve Martinelli UC Los Angeles

"There's no way I would have passed my Organic Chemistry class this semester without the notes and study guides I got from StudySoup."

Jennifer McGill UCSF Med School

"Selling my MCAT study guides and notes has been a great source of side revenue while I'm in school. Some months I'm making over $500! Plus, it makes me happy knowing that I'm helping future med students with their MCAT."

Bentley McCaw University of Florida

"I was shooting for a perfect 4.0 GPA this semester. Having StudySoup as a study aid was critical to helping me achieve my goal...and I nailed it!"

Parker Thompson 500 Startups

"It's a great way for students to improve their educational experience and it seemed like a product that everybody wants, so all the people participating are winning."

Become an Elite Notetaker and start selling your notes online!

Refund Policy


All subscriptions to StudySoup are paid in full at the time of subscribing. To change your credit card information or to cancel your subscription, go to "Edit Settings". All credit card information will be available there. If you should decide to cancel your subscription, it will continue to be valid until the next payment period, as all payments for the current period were made in advance. For special circumstances, please email


StudySoup has more than 1 million course-specific study resources to help students study smarter. If you’re having trouble finding what you’re looking for, our customer support team can help you find what you need! Feel free to contact them here:

Recurring Subscriptions: If you have canceled your recurring subscription on the day of renewal and have not downloaded any documents, you may request a refund by submitting an email to

Satisfaction Guarantee: If you’re not satisfied with your subscription, you can contact us for further help. Contact must be made within 3 business days of your subscription purchase and your refund request will be subject for review.

Please Note: Refunds can never be provided more than 30 days after the initial purchase date regardless of your activity on the site.