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

CHM 234| Epoxides and thiols

by: Alvin Notetaker

CHM 234| Epoxides and thiols CHM 234

Marketplace > Arizona State University > Chemistry > CHM 234 > CHM 234 Epoxides and thiols
Alvin Notetaker
GPA 3.33

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 is the material topic just before the second exam. So, this is not the full week of notes. I will upload it into the next set.
General Organic Chemistry II
Class Notes
Organic Chemistry
25 ?




Popular in General Organic Chemistry II

Popular in Chemistry

This 6 page Class Notes was uploaded by Alvin Notetaker on Saturday February 27, 2016. The Class Notes belongs to CHM 234 at Arizona State University taught by Pillai in Fall 2015. Since its upload, it has received 38 views. For similar materials see General Organic Chemistry II in Chemistry at Arizona State University.

Similar to CHM 234 at ASU


Reviews for CHM 234| Epoxides and thiols


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: 02/27/16
Epoxides    (On the last note when naming the epoxides, those names were wrong.)  Epoxides are not substituents, thus it does not get the same rule as other substituents like methyls  and ethyls. So when writing the prefix “epoxy”, the word goes before the parent chain’s name.    Preparation of Epoxides    Reagents:  ● MCPBA    ● Peroxyacetic acid      Preparation from Halohydrins  Reagent: halides with water    Reagent: strong base  ● To make epoxide    Mechanism:        []    Enantioselective Epoxidation  Select one of the two enantiomers.   Reagent:  ● Ti[OCH(CH​ 3​24​with (±)­DEM    (Sharpless catalyst)  ○ +: above plane  ○ ­: below plane  ● t­butyl hydroperoxide  Only with a​llylic alcohol    Chiral catalyst can lower the activation energy for formation of one enantiomers is more  effective than formation of both enantiomers.    The orientation when drawing the Sharpless asymmetric epoxidation, the hydroxyl group is at  the upper right corner.        Ring­Opening Reactions of Epoxides  Epoxides are ​more reactive​  than ethers because of the stress in the three­member ring in a  nucleophilic substitution reaction. The ring will ​open up​  as a result of reacting.    When the epoxides is unsymmetrical, the nucleophile will​  attack the less substituted​  position.  This will cause an inversion:      Acid­Catalyzed Ring Opening  Acid protonate the oxygen atom    When the epoxides is unsymmetrical, the nucleophile will​  attack the more substituted​  position.    This attack is an S​ N​2 reaction        Will attack  Dominant factor  1° vs. 2°  1°  steric effect  2° vs. 3°  3°  electronic effect  1° vs 3°  3°  electronic effect    Thiols and Sulfides    Thiol = ­SH  When naming, the compound ends with “thiol” instead of “ol”                   3­methyl­1­butanol                                          3­methyl­1­butanethiol  Thiols are also known as ​ mercaptans    3­mercapto­3­methyl­1­butanol  “mercapto” is used when thiols are a substituent.     Thiols can be prepared with a S​ N​ reaction with sodium hydrosulfide (NaSH) and alkyl halide.    Sulfides  Similar structure to ether with oxygen, ether structure with sulfur are called ​ sulfides or  thioethers.​                 diethyl ether                                        diethyl sulfide  Prepared by nucleophilic attack of a thiolate on an alkyl halide      SAM  S­Adenosylmethionine (SAM) is a good biological methylating agent  Same effect can happen with methyl iodine.    Methylation is the process of substituting methyl group into the molecule, replacing the  hydrogen atom.    Synthesis problem   


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."

Kyle Maynard Purdue

"When you're taking detailed notes and trying to help everyone else out in the class, it really helps you learn and understand the I made $280 on my first study guide!"

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!"


"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.