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

Notes for Week of October 12-16


Notes for Week of October 12-16 CHEM 2302

Marketplace > University of Minnesota > Chemistry > CHEM 2302 > Notes for Week of October 12 16
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

As always, I strive to bring you the most thorough notes possible! Enjoy!
Organic Chemistry II
Dr. Taton
Class Notes
25 ?




Popular in Organic Chemistry II

Popular in Chemistry

This 16 page Class Notes was uploaded by EMMYSOTO on Sunday October 18, 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 16 views. For similar materials see Organic Chemistry II in Chemistry at University of Minnesota.

Similar to CHEM 2302 at U of M


Reviews for Notes for Week of October 12-16


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: 10/18/15
Hydrides as Reducing Agents Lithium aluminum hydride LiAlH4 is a strong reducing agent It will donate hydride H39 to m CO containing functional group Examples 9 OAIH3 2 30 O OH 1 LIAIH4 or JUSt H20 R H R H R H H H aldehyde primary alcohol 6 O 1 LiAlH4 OA39HS 2 H20 0 gt R R39 R R39 R R39 H H ketone secondary alcohol Hydrides as Reducing Agents Lithium aluminum hydride LiAlH4 is a strong reducing agent It will reduce almost any CO containing functional group to an alcohol Example 6 O OAIH3 OH 1 LiAlH4 2 H20 R OR39 R H R H H H ester one and then another equivalent 0 equivalent adds of H adds i unavoidably R H Reduced by O O O O O LiAH4 to an alcohol RAH Ri R RiOH RiOR Rim aldehyde ketone carboxyic acid ester acy halide letiVl chug MS extra 3mm 9 339 e c 4 c o gtc c o HGch gt H zoe k NHL 1 L does not schwill cxis39l 39 gt W is L Mob is amtuquot w Mimi le H a L39 n 19 l9 H H 39l H r3 D39sLTH a A39IQB H H H H H D H 1 H N19 H H Alba1 Q0 L in his c554 50 comml rushtn h at39ull ckw l w had in rush advers wm kw um LsAnI mas wa Imam G 4 LI Ale H CH3 39 a HO 0 e H c 39 9 2 H l Rig 53 H10 MAI F Xmas n z 6 ANDquot H uh CH3 H3 Eslm as Stu ns Nutaria L363 Lia 56 n Q g H Q m H H N 39 Tm quot429 0 r I 39 H H I can com cH3o A19H H G 0 CH3 H H cnzoqI H gt quotac 0 gt H O Pil H 391 Lie cage I L 9 9 Q n AlH H A0H H B Q 39 oH H H 9 il HAl H l LIAH39II39 Double Addition of Hydride to Carboxylic Acids and Derivatives Why 05 05 Ketones and aldehydes are more J 5 electrophilic than acids esters and 5 R R R OR acyl halides u As soon as a ketone or aldehyde is generated it is immediately reduced Lone pa donat on by oxygen reduces partial agam39 positive charge on CO carbon Reduced by O O O O O LiAH to an alzoholi RAH RA R39 RJKOH RiOR39 R C aldehyde ketone carboxyic acid ester acyl halide Hydrides as Reducing Agents Exception LiAIH4 reduces amides to amines Examples 0 1 LiAIH4 H H Mechanism depends i gt 4 slightly on whether R NH2 2 H20 R NH2 Zide has an NH or But the result is the O 1 LiAIH4 H H same 4 R NR392 2 H20 R NR392 Reduced by 0 o o o o LiAH to an alzoholi RAH Ri R39 RiOH RiOR39 RiCI aldehyde ketone carboxyic acid ester acyl halide Hydrides as Reducing Agents O NaBH4 OH NaBH4 isn t as basic as LiAH4 EtOH so reaction can be conducted in i gt protic solvent and separate R H R H H workup step isn t essential aldehyde primary alcohol NaBH4 O EtOH 0 L I RI Rk t R R H O 0 e one secondary alcohol RAH RA R39 aldehyde ketone Biological Cofactors as Redox Agents LiAIH4 isn t used in biology but biological reductants are mechanistically similar NADH reduces by acting as an H39 donor enzyme H3C H3C gtO H 09 H R H NADH a NAD derived from niacin Vitamin 83 Cofactor A smallmolecule helper that is required by an enzyme to catalyze a reaction Many vitamins are cofactors l 8 1 539 2 ab 3amp2 233 D I 2 IV D i u oloO ml 1 I o 3968 mws 224 g E kit khm 79 99 0 2 at t 9 ti n2 a 791 Ana 034 SDLeRA 95 LKFTJtm Goof IL 1 Wamp K Sterically Hindered Reducing Agents Stop At Aldehyde 1 gt H lt AIHAI Chapter 22 O gt D B ALH r Rim 2 ester w b o quot20 0 A ow 9 3dlt A R OH L 3939 R H carboxyic acid Li H AId O aldehyde 0 L9 fr X Chapter 22 R 039 LiAHO tBu3 acy halide 3978 C Nucleophiles Approach Carbonyl Groups At An Angle Nuc O Nucleophiles are electron donors R 0 71 2 quot1320 As a nucleophlle approaches R1 0 D the CO electrophile it will donate electrons to the most available lowestenergy Nugo molecular orbital the LUMO Optimal overlap with the 75 LUMO is at an angle above or below the CO plane R2 II H quotC O TE R1 3 A A A1 H 54 3quotquot 39 r LWw z quot0 39 WV into AldLh d1 1 mud 1 LIA 0 MB HI 78 o I Vtgw A A A quot134quot I 04 H m IL OH IL H 4D RX Oxidation V V l Aaio N93 quotSwarm Oxid oh H L 339 quot3 quot510 011 quot150quot Hz 6397 0quot was catalde I39v kw FWWJ diuctiou COM 5 CALtalqu M411 mast divaH0quot Nucleophile Additions to Carbonyls Generate Racemic Mixtures 939 addition to H H AI H top face Ill szw 0 R R 0 75 2 Ill10 R1 6 b addition to R1 939 7 bottom face R2 06 H H 5050 mixture of top and bottomface adduct is observed Enantioselective Reduction of Ketones Using Chiral Catalysts Chiral catalysts bring reactants together in specific geometries to force the preferential formation of one enantiomer over the other Example 0 1 BH3 HO H SCBS reagent lt CH3 R CH3 n u Ph RS g Ph RL 8 0 Reaction NB generates this enantiomer only k CH3 2 H workup Enantioselective Reduction of Ketones Using Chiral Catalysts H230 H 3 BH3 N O B Eh V KZHzo CH 3 SCBS reagent Hydration of Aldehydes and Ketones acid or R b t d ase ca a yze OH R H OH H a gemdio hydrate Steric hindrance electron donating groups destabilize hydrate H Keq2300 H OH gto H20 F gtlt H H OH H3C Keq 0002 H3C OH H x A x H3C H3C OH Acetals and Ketals H3C H3C OH H3C OH gto CH3OH 4 gtlt gtlt OCH H3C H3C H 3 a hemiketa a hemaceta acidcatalyzed H3C OH only quotI30 OCH3 gtlt CH3OH 4 H20 H30 OCH3 H3O OCH3 a keta H3C Under conditions where H20 can be selectively gtltOCH3 removed equilibrium driven to ketal OCH3 H But it s still entropicaIy uphill 3 molecules used to make keta H20 an aceta IJWL Hom 6F 30 H20 310 3 HD c oH E NmDst aims I 60 tL leek ham M ML X f i0n5 Mm catahgsf C H CH3 an E 3 F I 3 x HZO39 CQS 13 O 3 OquotI 9 uo il on H CH H H I a H o 3 H H H quot fs Fov alnwuivx acid anal base Car al zeal Muhmisms Auoid drmfng iwkumdiodrcs Cowlaiming LOH os39vb39wc ma atrim ions zwi uims quot In acid tn to Arm 0M7 PoSiEULH chmgtJ madmama Do dais gt7 ProtbthMS 5quotch 39tkad wou39d oHMvwist Lccom omI39OIAS 39V 5W 477 1396 drama only dialJ druwa intumdims D dais 5391 Fatwatins sites had39 would O HWWiSL buoml Iakw 0 ll lust Cawvs39t o F eocoe 6 m9 39cke H3 1169 gt 0 5 0 0 0 0 J cHs H H3C Cquot3 0 Ho tkoe Hoe AcctAIS M045 u a l ale Ex H35 Kmcl H3c 9 H36 3 Hsc OcH s gt D A X H c O H C I 3 DH 3 3 3 039 c CHSBH A quot5 Wikutal vmsFovmaEioh bF MihLEA 399 Illrt V 1WV 5 M EX 5N1 mchmism Cyclic Acetalleetals HCI 0 catalyst O O k HOVOH F H20 So ketones and aldehydes can be reversibly converted to ketals and acetals relative HOVOH HCI reactivities O l aldehyde k 0 gt R R R R ketgne H20 HCI ester Cyclic Acetalleetals as Protecting Groups Protecting Group A modification that protects a functional group from a synthetic operation it would not otherwise survive Example 0 0 how OCH3 gt OH HO g HCI O 04 O 1 LiAIH4 OCH3 Some Common Protecting Groups OH A 0 VA i H20 HCI O C gtAgZO Br H2 H3C Protects against Bases nucleophiles reduction oxidation Bases acids elimination H3CSiCquot Et3N Bases acids H3C CH3 nucleophiles OH O Si reduction oxidation Bu4N F39 CH3 The WIttIg Reaction R R39 R R H gt gtlt gtlt x H H H H R39 minor primary aldehyde halide or ketone X CLBFJ Ph3PO H H 1 1 PPh3 R R39 3 T olt R R Ph P o6 G 2 nBuLI ea 3 a PPhg gt egt FgtPh3 gt H H H H H R R39 phosphonium betame yide The Wittig Reaction The lesssubstituted carbon of the alkene must come from the alkyl halide how would one synthesize H3C H30 00 O H gt H lt H H3C A A Br 5 Lp mg


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."

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.