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

Lecture Notes from 10/5-10/9


Lecture Notes from 10/5-10/9 CHEM 2302

Marketplace > University of Minnesota > Chemistry > CHEM 2302 > Lecture Notes from 10 5 10 9
U of M
GPA 3.46
Organic Chemistry II
Dr. Taton

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

My lecture notes from last week for Taton's class. I took them right over the slides so that they are available for reference. I hope they help!
Organic Chemistry II
Dr. Taton
Class Notes
25 ?




Popular in Organic Chemistry II

Popular in Chemistry

This 8 page Class Notes was uploaded by EMMYSOTO on Sunday October 11, 2015. The Class Notes belongs to CHEM 2302 at University of Minnesota taught by Dr. Taton in Summer 2015. Since its upload, it has received 21 views. For similar materials see Organic Chemistry II in Chemistry at University of Minnesota.

Similar to CHEM 2302 at U of M


Reviews for Lecture Notes from 10/5-10/9


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: 10/11/15
Mcdnmisms 9 f1 39 HO 0 gt HOc lt V I WWSAL39L What is 39UM AimeHow oF 7mmbvium7 39 Eyrth MOVE more molecuus 50 equilibrium lus to W lLH 970 WSL WW 41N 43726 AM Will bl couwin oolau1 lavhumans om kss stuola ale mosl nut ve usz 5P3 hlemoiize Organometallic Reagents are Synthetically Equivalent to Carbanions R Li alkyllithium organolithium R Mg Br Grignard reagent organomagnesium halide R CEC Na alkynylsodium Computed electronic structure of CH3Li All of these react as R9 Generating Organometallic Reagents 1 Deprotonation Not common Works for alkynyl some Sp2 anions but not for sp3 because alkanes are not acidic enough Examples CH3 CEC H NaNH2 gt CH3 CEC Na NH3 hexane OIquot I N BuLi O N L39 Etzo c9 cyo gt CL 39d39e I 1 9 e E L Alkoxiau HzcCH2 L39 gL5 I Ex 9 CHs cac H NH 7 quot Hag LEC NA NH3 A 39M A PM 25 Agnian PM 35 Generating Organometallic Reagents mosl comvnon wowI 0 saturate orjmomtalic my L s 2 Metalation of an alkyl halide Common for Grignard reagents sp3 alkyllithiums Examples CI 39 39 EtZO mm I IVI93 I I I I I I I I I I I I I I Br hexane L39 I 2LIs LiBr quot39l violaH1 l solid l 33 I Generating Organometallic Reagents 3 Lithiumhalogen exchange Common for sp2 alkyllithiums Not useful for sp3 alkyllithiums Example imrei l not LiBr commerCIaIIy commerCIaIIy available available Reaction is driven by 6 formation of more more stable 9 stable carbanion A than A Reaction of Alkylmetals With CO Bonds H 1 R MgBr gtO gt H H e Ro 2 H H gt ROH H Ketones and aldehydes are more electrophilic than esters and acyl haHdes H r 5 formaldehyde primary alcohol 3 2 E RI 1 RI 6 2 H RI 63 RLi gto gt RO 39 gt ROH g H H H gt i aldehyde secondary alcohol E a R39 I U 1 R e 2 H R R Na O gt R o gt R OH RII Rquot Rquot ketone tertiary alcohol Double Addltlon of Alkylmetals to Esters and Acyl Halldes R39 R39 1 R Li R39 e 2 H R39 gt or O R O R OH CI CH3O R R an acy ester chloride One Ru and then another equivalent of gtO equivalent adds RLi adds R unavoidably 5 8 Why k 8 RJKR R39 AchHo Lone pair donation by oxygen reduces partial positive charge on CO carbon 61 H IL 09 M cl L 039 3zHso H H Workuf39 Stdf AllwxioU haw 4mm n3qu boa L watt 4 Mala Primwnj alcohol a QB I Coe 2 I430a H L39 39I39 gtLHr39o I woka J 0H AldLHdL Alluxidk cec ws m9 W 9 Ho C I Hsc csc Na Lgt 9 Z wow OH Alcohol Ketones from Lithium Dialkylcuprates Synthesis of dialkylcuprates Li Cul R39C gt R39Li gt R39ZCuLi orithium halogen exchange Addition of dialkylcuprates to acyl chlorides R SOCI2 R R39ZCuLi R gto gt gto gt o HO on R39 Unlike other alkylmetals cuprate adds only once Carboxylic Acids from Alkylmetals Grignards and CO2 Open Epoxides 1 co2 O 1 R MgCI R MgCI L CH3 L CH 0 3 o6 4lt RN R De H3C CH3 OH 0 2 H3O RN 2H30 R4 lt 39 OH H3C CH3 Another way of making new CC bonds with alkylmetals Cl CHI 6 Jig LI z N L 2 fm hr OH O O 3634 I in lust


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

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!"

Amaris Trozzo George Washington University

"I made $350 in just two days after posting my first study guide."

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."


"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.