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

326: Organic Chemistry - Study Guide

by: Andrew Ghobrial

326: Organic Chemistry - Study Guide 326

Marketplace > Stony Brook University > Chemistry > 326 > 326 Organic Chemistry Study Guide
Andrew Ghobrial

Organic Chemistry
Prof. Fowler

Almost Ready


These notes were just uploaded, and will be ready to view shortly.

Purchase these notes here, or revisit this page.

Either way, we'll remind you when they're ready :)

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

Organic Chemistry
Prof. Fowler
Study Guide
50 ?




Popular in Organic Chemistry

Popular in Chemistry

This 2 page Study Guide was uploaded by Andrew Ghobrial on Wednesday October 15, 2014. The Study Guide belongs to 326 at Stony Brook University taught by Prof. Fowler in Fall. Since its upload, it has received 197 views. For similar materials see Organic Chemistry in Chemistry at Stony Brook University.


Reviews for 326: Organic Chemistry - Study Guide


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: 10/15/14
CHE 326 Studv Guide 13Diene Svntheses Chapter 13 Solomons and Fryhle discusses conjugation and various reactions of 13dienes The reactions include the very important DielsAlder reaction which features the reaction of a 13diene with an alkene to give a cyclohexene ring 30 E An example of a Diels Alder reaction 0 AK In CHE 321 we discussed various ways to make alkenes but we did not discuss methodology for making dienes Fortunately we can apply some of our standard CHE 321 reactions to this important problem 1 Elimination Reactions to give 13 dienes Here are some simple examples VOK NBS 6 CH3 W In A a vinyl Li reagent is added to a ketone to give an alcohol Acid catalyzed elimination will give the most substituted and thus most stable diene In B Free radical bromination at the allylic positions gives a tertiary bromide Elimination with hydroxide gives the most stable diene Elimination with a hindered base gives the most accessible isomer In special circumstances we can make a diene via a double elimination reaction Br 39Br Br Br This works in the case C of cyclohexene because the alternate alkyne product would be too strained But it will not work in an acyclic case D because the preferred product will be the alkyne not the diene ll 2 Dienolates Here is a special synthesis of a diene involving enolate chemistry 7 0 CSiCH33 o 39 E JVW V We know that a ketone is is equilibrium with its enol form 0 OH ax If we add a trimethylsilyl chloride TMSCI and a base like triethylamine NEt3 we can trap the enolate with the TMS group This TMS protecting group can be removed at some later time in a reaction scheme Later in the course we will add additional methods of 13diene synthesis Don t worry about them now 3 Organometallic Coupling Reactions These reactions are discussed in Special Topic H pages 1016 1017 4 Wittig Reaction This reaction is a very useful method of making alkenes it can also be used to make a diene It is discussed in Chapter 16 pages 711715


Buy Material

Are you sure you want to buy this material for

50 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

Jim McGreen Ohio University

"Knowing I can count on the Elite Notetaker in my class allows me to focus on what the professor is saying instead of just scribbling notes the whole time and falling behind."

Allison Fischer University of Alabama

"I signed up to be an Elite Notetaker with 2 of my sorority sisters this semester. We just posted our notes weekly and were each making over $600 per month. I 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."


"Their 'Elite Notetakers' are making over $1,200/month in sales by creating high quality content that helps their classmates in a time of need."

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.