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UA / Chemistry / CH 232 / What is the oxidation of aldehydes?

What is the oxidation of aldehydes?

What is the oxidation of aldehydes?

Description

School: University of Alabama - Tuscaloosa
Department: Chemistry
Course: Elem Organic Chem II
Professor: Dolliver
Term: Fall 2016
Tags: Organic Chemistry
Cost: 50
Name: CH 232 Test 2 Study Guide
Description: This study guide includes a reaction list with examples, a "Trends to Know" list, and a "structures to know" list. The "Trends To Know" section covers Nomenclature, how to drive a reaction one which way you want it to go (ie towards an acetal vs towards a ketone), Oxidation/Reduction, physical properties of carboxylic acids and their derivatives, how to make CA's, etc, etc.
Uploaded: 09/30/2016
14 Pages 16 Views 7 Unlocks
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TE


What is oxidation of aldehydes?



TEST 2 REACTIONS LIST

CH16 TEST

14 Hydrations greater for aldehydes than Kerones

HEH + HOT HOH

15

Addition of Alcohols to Form Hemidcetals

W

hzoda oh no siroh

16 Addition of Alcohols to form Acetats


How does lialh4 reduce?



0+ Но он H, K + H,0 17 Addition of Ammonia di rts derivatives. Formation

06 Emines

NO + H2NCH3 H3 -NH3 + H2O

SRL

PO

18 Addition of 20 Amines: Formation of Enamines

I JOTH-ND H ON +420 19 Addition of Hydrazine&its derivatives


What is the wolff kishner reduction?



Ot H2N-NH2 YEN-NH2 + H2O

20 Keto-Enol Tautomeriem We also discuss several other topics like What did the kellogg briand pact do?

ОН (Наса, Нас=H,

keto enor 21 oxidation of an aidehyde to a carboxylic aud

DTH15420, NAOH

COH +Ag

CH +A920 2)120gHU

NaClO2

NaH2PO4 2-methyl 2-bultene

Stud

22 Metal Hydride Reduction (LAH, Nalety) If you want to learn more check out Describe comparative advantage.

t

o

oNa Bottega We also discuss several other topics like What is an x company's estimate of monthly fixed factory cost?

on Cracomic)

2) H20 23 catalyho Reduction

(eo + H, Pt ( If you want to learn more check out What are the competitive conditions in food service?

ГТОН - 25°C, zatma 24 Reductive Amination Han-CHE

NaBHz CN 4 + CH3NH2 Meat ? Don't forget about the age old question of What is the chemical structures of plasma membrane?

25 Clemmensen Reduction

OH O pih zn cha), HU,

E

N

26 Wolfe Kushner Reduction

KOH + HNNH, Diethylene

TNMT2 glycol

+ N2 + H2O

27 Deutorum Exchange @ an d-carbon

Due | CH 3 C CH3 +6020 De D2 C CD 3 + GHOD 28 Halogenation @ dn X-carbon

+ Brz Chacool Brther [417 29 Acidity of carboxylic Acids

CH3COH + H2O7 too + H200 kg=1.747105

- which side is favored? 30 Ryn of carboxylic Auds w BaCES If you want to learn more check out What defines a show?

O COOH + NaOH Hyos conq@ + H2O

Stud

o cooHt+ Nilz H20? OONHqQ 31 carbonation of a Grignard Reagont

rymg Br 12 Cook + Mgzt

- 2) HU/H20 32 Industrial Prep of Aceto Aud by the carbonylation

of methanol

CO+ 2H2 catalyst, CH30 H Thoduemit CH3COH

HI, H20 33 Reduction by LAH

Он-он 1) Li АЛҒч л ан, он

2) H2O U 34.Fischer Esterification

YOH HON HsOy or +H2O 35 Rxn we digzomethane

n ot + CH3 ether notzt Ne 30 conversion to Aud halides

M OH+ soce, ether nice+soce, the 37 decarboxylatron of B-keraacids

& co warm & con 39 decarboxylation of p-decarboxylic acids

heat HOCCH2COH H2OOH + CO2

CH18

-

39. Audity of Imides

farver

NH + NaOH →

og format in vele annonces

No Ngo + H2O

imides>amines audity bc (mide stabilized by resonance

Studio

Nao

40 Audity of sulfoamides

S-M-(CH3)4 CH, ENQOH → 4 Hydrolysis of an Aud chionde

S-N-(CH2CH3 + H20

Н.Сck + H,0 -> Ч, он * {% 42 Hydholysis of an Aud Anhydride

CH3COCCH3 + H2O CH2 COH + HOC CH2 43 hydrolysis of an Ester

Laad catalyst -base required in equimolar amt

CH2CO + NaOH H CH 2 COO NGO + HOO 44 Hydrolysis of an Amide

pokon 1400 treno a lot wing

CH?@wat mooi om odwar Hum @ 45 Hydrolysis of a Nitrile

of CH, CEN + 2H20 + 4,504 Hey HČOH + NH4@Hsoqol

CHACH,29 CEN? HYD + NaOH FT CH (CH), 80 NB 4 Niz 46. Rxn of aud chronde wf Alcohol

Na Hoong the 47. Rxn of an Aud Anhydride wf Alcohor

CHE Colche HOEP 7 CHŁOct + cf&OH

the

SENSO

481 Ryn of an Ester wy An Alcohol Transesterfication

OCH3 + Hon Hellon + CH3OH 49Rxn of an Aud chloride wy Ammonia or an Amine

Mice + 2NH3 M NH2 + NHyce 50 Ryn of an Aud Anhydride wy Ammonia/ Amine

CH2 COC CH3 + 2NH3 CH3 C NH2 + CH3COONHY Si Ryn of an Ester wy Ammonial Amine

. Ph

i

| y^OC + NH4 N H, +C07 52 Rxn of an Aud chionde wf a CA sait

CHece + NaOge - HC & C + Nascio 53 Rxn of an Ester wy a crignard Reagent

2 Ermger HQET syrome 2 H,0,Hce o 54 pxn of an Aud chloride wy a lithium Diorgan ocuprate

i OCCH3), Uli, ether; -78967 w

ce 2) H2O 55 Reduction of an Ester

- W LAMHY CLAH) I Ph i Li Alty, ether phy

YouHz 2) Hyg, HCE MOH

OH + CH3OH - w/ DIBALH

OOTBALH, toluene, 1867

m u ch of -OCH2 2 H2O, Hle 56. Preduction of an Amide

- DLiAlly

NH2 2 0

m NH2

SOSO

57. Reduction of a Nitrile

YON ID LiAllty, ether

Br 2 H2O

JSOU

Study SONO

TRENDS TO KNOW ONTD. TEST 2 MATERIAL

CHIO

Addn Of Oxygen Nudeophiles Who R POOR

hemiacetal duetal - to drive to acetal

Ouse excess alcohol

itt cat RO OR -c- t R-O-H2

q + H2O (excess) euse nonnudeophilic anion like H2504 or HOTS - to drive to Ketone use excess water

su Htcat RO OR HO - c- tp-O-H e i + (excess) bo Protection

- Ketones

R

R

s

Br + 2R1-0-4

T

A protection

Br

e Ing, ether

RP.

Che

Cours om

1 Loopis

n mg Br

COM

Stue Sour

AsOH, HO

de-protection

-alcohols

Hover

) His brothers Bring och MC EA

Study

HOLHO

1 + OH HG-C-H

H2 C-C-H

OH

Nitrogen Nudloophiles -Istart wy where R

H-N-R L

Product imihe

H

NCH I

FN-H

hydrazone

TI

LE

semicarbazone

NE

6

oxidation -aldehyde--> Carboxylic aud using Oz (slow), Hygrou, KMnOy of Ag*') Ag,O, Tollen's Reagent CAgNO3+ NH3)

Studs sou

-ketones-> carboxylic aud using powerful

like konoy

ů o H-

OHOHHO

G

Reduction -LiAllty most powerful hydride donorbe - Al is large 'H's aren't held as well to it

• Ketone 20 alcohol

aldehyder jo alcohol CA lo alcohol

ester > diconot

ud SON

|- NaBHY

• Ketones 20 alcohol aldehydes + 1° alcohol

esters> NR

• CA'S NR - H2, PP/PT/Ni @zatm

o carbonylst aiconors

2 H2 Nicat U zatm T - H2, Rh

• alkene alkane

OH

*reduces alkeno alco

u

H Rh

u

-reductive amination

Ketone amine

modified bonohydnde =NqBH3CN Clemmensen Reduction

aldehyder kerone-alkane

• reagent - En CHg) in te -Wolff-kyschner Reduction

Aldehyde Ketone7 alkane o reagente N-AM

ECH 17

by carboxylic Aud Nomenjature

compound

common

formic H-C-OH

acid

SHOU

IUPAC methandic

acid

CH2 C-OH

acercaud

ethanoic acid

Study

ampd WNIO

common

Propanoic

acid butync

acid oxalic caud

TOPAC

propanol

aud butanoc

CH3CH, C-OH

CH,C4, CH, LoH

H0-88-OH

ethanedioc

aud

SER

ABOUT

H0년대는 4에

malonic

aud Succini

FIN

liauds/

aud

SESH

PE

glutan - aud adipic - acid

Pimelic

aud \xpneumonia for diauds: Oh My, such Good Apple pie

more complicated

cmpd biologists I common I TUPAC

|(5)-2-faminopropanot

(5)-2-aminopropanaia aud

L-alanine

HO

1p-kofobutyrte

acid

3-oxobutano

OH

acetoacetic

aud

4 Physical properties

-high bup.

inanitely soluble in H20 - low MW CA's smell bad

Study Soul

Stud

How to make ca's 1-oxidizers

aldehyde + CA olo alcohol [O]/ H20 aldehyde [03/19, CA

• alkyl halide Greghard Co, hot, CA 4 Fischer esterification

Atal Ht, ester - to drive to ester remove Ho or add lots of all Lo Nomenclature of CA derivatives

compound I common

I IUPAC benzoic

benzoyl aud

chlonde

CH 18

reu

aconc

anhydride Othyl

quotate

Olhano methanol

anhydride ethyl ethanoate

of

TE

5 pentolactone

TV

(S)--butyrolactone

(S)-3-butanolactone

.

-N-CH3

CH2

N,N-dimethyl formande

DMF (Solvent) (5)-3-butanolactam

(S)-ß- butyrojactam

uydic anhydride

Succinio

anhydide

4. Acidity

|--Sulfonimide-succinimideamide audity

CA delvis gs LGSăreactivity to nucleophilic subosh tution Cbased on elim & addn stops? -aud halides> anhydrides> ester/ amides

Stuen Sour

SEASON

Stud

STRUCTURES TO KNOW ... TEST 2

a hydrate

g hemigietal HOOR

-

R

an acetas ROOR

Sad Sou

H-0-0-0-H

HOTS

amine

dihydropyran

O

H-O-5-

CH3

an imine/ Schiff R-C-R base

an enamine R-N-R

enolate ion

R-ċ-ċ-CR

LAHELAL Hy

boron sait

NaBlly Nacht

H-Al-H

H-O-B-0-H

OH

acetone

vinegar

ranud milk

caproic and

Ден

сон

сон

Study Soup

drazomethane

aud haride

R-c-X

anhydride

ester

amide

sulfonic aud

Study SOUL

RS-OH

R-E-O-ER

R

-C-0-R

RC-N-RCH)

RCH)

Stud

a sulfonyl chloride

p-toluenesulfonyl chlonde (TSC)

pyndine

EtzN

w

DIBALH7 diisobutyiqluminum

hydride

Et

Et-N-ET

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