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UCONN / Chemistry / CHEM 2241 / What is the example of carbon nucleophiles for addition reactions?

What is the example of carbon nucleophiles for addition reactions?

What is the example of carbon nucleophiles for addition reactions?

Description

School: University of Connecticut
Department: Chemistry
Course: Organic Chemistry
Professor: Anwar beshir
Term: Fall 2015
Tags: exam, 3, study, guide, organic, and Chemistry
Cost: 50
Name: CHEM 2241 Study Guide Exam 3
Description: These notes cover what will be on Exam 3 on Friday, April 22.
Uploaded: 04/18/2016
6 Pages 61 Views 3 Unlocks
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What is the example of carbon nucleophiles for additions reactions?



Guide Exam 3

Makina Olt a Good Leavince Group E to make olt a cood leavincs Croup, protonate it by addince

- Ht to make it H2O

It will then be able to partisipate in substitution

OH

Y + HBr > -And Elimination Reactions. Addinc H2SO4 or H3 PO 4 will


What is the carbonyl compounds?



alexeys lead to elimination. Elimination reactions prefer to go through a tertian alcohol - if tertiary, Es is prefered. If you want to learn more check out What are the functions of foreign corporations in the us?

-

+ H2O

Stud

#250.

HO

CEC

C=C

+ H2O - I acts like a base, took alt soa double bondcould form


What is the electrophilic aromatic substitution?



CH3

Trans-Major oletess stenic hinderence

Cis-minor ble more storic

hinderance

to, you could add PBro to make OH a good LG

D

-H Don't forget about the age old question of What is the function of desegregating public transportation, montgomery, alabama?

Br-P-Br ->

~

COR PR

-

>

B

+ H3PO,

for add SOCIz or make it a sulfonate ester R-$10%, like: We also discuss several other topics like How does air pressure depend on height in the atmosphere?

CHS De Choice as a sci

FA weaker base is a better leaving Group, and therefore more

reactive.

Ethers B-O-R

If breaking a bond on either side of the oxygen would result in If you want to learn more check out What is the male­ sex-role identity paradigm?

a tertian, carbocation, then do Sul. The nucleophile attaches to the carbocation & the O is protonated

Soup

HES

stua

If breaking a bond next to Oxygen results in only pamainy and methyl Don't forget about the age old question of In economics, what are the types of product differentiation?

carbocations, then it coas through SuzO is protonated the bond to the least stable carbocation breaks, the nucleophile attaches to that. Don't forget about the age old question of What species was selam, and how old is her fossil?

1

x

H Bry

OH + Br-CH3

CH3

Stud

Epoxides - In acidic conditions: H protonates 0, and the Nu will attack

the carbon attached to o that is more substituted, and has sever hydrogens.

er + H-Brz

If basic conditions: The nucleophile attacks the carbon that

is less Substituted, t has more hydrogen. Then Ois protonated

voo + CHOH CH s Nao) LOHocha

"Be

Occhiametelic Compounds - The carbons take é from the bond with the metal and acts like

ananionic naxleophile. Methyl is the most stable, tertiary is the least stable.

^ Br + 2li

hexane

LiBr +

/

IR Spectroscopt -Lichter atoms + Stroncsec bonds have higher frequencies

Amines - lamines have 2 spikes, 2 amines have I, + 3° amines have none

Soup

3500

3000

3500 3000

3500 3000

R-N-R

H-N-H

H-N-R

y Sour

OH and Carbonyl Groups -

•Carbonyl Group X-Sharp Spike around 1700

• OH croup - broad oval above 3000

· Carboxylic Acid Jou-Spike at 100, and ovalis brodert closer to smo

mot

LOH

Stud

CH bonding - sp is before 3000, sp2 is just before 3000, and Sp3

is just after 3000

sp?

3000

3000

FA molecule with resonance cuill bave a slightly lower absorption spectan

Electrophilic Aromatic Substitution

If civen benzene with no substituents, any I could be replaced

by an electrophile If benzene has an Electron Withdrawing Group attached, then

an electrophile can only attachio a metal position - except for halven EU

ENG: 3-C-R.-NO

NO,

NO2

HNO3 H2SO4

I T

a NO2 If benzene has an Electron Darretina Group attached then an electrophile

can attach in Ortho or para positions. Halogens also follow this rule, even though they are EWGs

· EDG: -OR, -OH4, -NH2, -NR, , -R.

OCH3

CH2

StSoup

OCH3

H2SO4

SO3H

) Stue

FEDG are more reactive than benzene, which is more reactive than

Ewls. Halocens are more reactive EWGs. -Friedel Crafts Acylation in

• An acyl group carbonyl replaces H

AlCl3 H2O

o

ri Aters

AICI

Stud

- Friedel Craft's Alkylation

· An alkyl group replaces H.

+ ATCT3

+ HCl

Nucleophilic Aromatic Substitution -To do this, you need at least one EWG, a cood LG in ortho or

para position, and a nucleophile to add._ If the conditions are not met, the reaction will not accucoccuill be

EAS. If electrophile instead of Nu-EAS. If LG in meta Ne-norxn.

Br

OH

+ Br

NO2

Carbon Compands

Addition Reactions - Nu is added to carbonyl carbono takes the

e and is then protonated. If it has possibility of resonance it is Stroncser base t reacts more easily

Soup

-

+GOH

Ą

HOO-H

) Stue

Substitution Reaction - There is a LG attached to the carbonyl

carbon, t it is replaced by a Ne

0

--

+C1

SH

+ SH R Ch. SR cil - Reactions at the a-Carbon - The most acidic a-H is taken by a

base. The most acidic H is the one without which the compound

can do the most resonance

0:0 te + :80 Retr<->te + H-BA

Stud

ait

H-B

1 Ketones R&R are more acidic than esters R ochs ?

Addinge nucleophiles to carbonyl croups

if a strong nucleophile is used-add Ne ist, then pootorcate o

4 t.Nuo

Ho Ho No

2 R R = RR if a weak nucleophile s used - protonate o, then add No

O-H i Nor No OH

+ More methyl groups = less reactive bkc less space to react - More electronegative substituents = more reactive

Excimples of carbon Nuclrophiles for Addition Beactions - Gricmard Reassents to makes 1,20, or 3° alcohols

CH3CH2-MOBc + H H -> CH3CH2CH20. + HGS > CH3CH2CH2OH -Acetylide Amions as Carbon nucleophiles

Soup

HCL

H-C=C. Na tr

stua

-Adding Hydrogen

Cyanide

:0

ESA

+H-CEN: F

애 CHz-C-CEN:

CH3CH + :N=C: -

-Phosphonium Ylides

The Chs attached replaces the =0

7

+ Ph, P=0

Stud

- Adding Hydrogen Nucleophiles

Li Al Hu and NaßHy donate a Ht

NaBity HOH

o

Nasty

CH

H2O

R

>

CH3

Substitution Reactions of Carboxylic Acids caith Leaving Groups - The weakest base is the best leaving group A nucleophile cuill a Hach more easily if the LG is more electronegative,

if the structure can resonate;t if there isn't a lot of steric Mindecance

TAO

No

i 6°

PNo | -26 is replaced by No, making it a carbonyl group again

o

R

LG title_

Stue Soup

stua

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