chem 3331 mega review stuff (1)

7/23/2019 Chem 3331 Mega Review Stuff (1)

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Reactions obviously covered in class

Radical Halogenationa. Go back to 4.3 to review this reaction

Allylic Brominationb. Allylic positions are those which are next to a carboncarbon double

bondc. Highly selective! only the most stable radical is "ormed through

resonanced. #aitsev$s rule says that the most substituted product is the most stablee. %ommon reagent&solvent' (B)

".

)n*g. (ucleophilic substitution! bimolecular! one step! transition state exists!

in the transition state! a bond is partially "ormed with the nucleophile

+backside attack, and a bond is partially broken with the leaving group

+no intermediate,! )-R(G nucleophile neededh. Reactivity' %H3/010*

i.

2.k. actors aecting )n*'

i. )trength o" nucleophile +secondary "actor,1. -rends in nucleophilicity

a. A species with a negative charge is a stronger

nucleophile than a similar neutral species. 5n

particular! a base is a stronger nucleophile than its

con2ugate acid.b. (ucleophilicity decreases "rom le"t to right in the

periodic table! "ollowing the increase in

electronegativity "rom le"t to right. -he more

electronegative elements have more tightly held

nonbonding electrons that are less reactive toward

"orming new bonds.



c. (ucleophilicity increases down the periodic table!

"ollowing the increase in si6e and polari6ability! and

the decrease in electronegativity.ii. )i6e and 7olari6ability +secondary "actor,

1. 8ore polari6able atoms&molecules are better "or )n*iii. )teric hindrance +primary "actor,

1. 5" we want a species to act as a base! we use a bulkyreagent like tertbutoxide ion +9*,. 5" we want it to react as

a nucleophile! we use a less hindered reagent! like

ethoxide. :ess branching! less steric hindrance.iv. )olvent eects

1. 7:AR 7R-5% solvents ; acidic hydrogens +H! (H

groups,*. 7:AR A7R-5% solvents ; anions are not as solvated!

enhanced nucleophilicity! better "or )n* +ex. Acetonitrile!

<8! acetone,l. )ubstrate "actors in )n*

i. :eaving Group eects on substrate1. Good leaving groups must be electron withdrawing to

create partial positive&electrophilic carbon*. :eaving group must be stable +weak bases! meaning

bases o" strong acids,3. :eaving group must be polari6able

ii. )teric hindrance o" substrate1. (ote' when comparing to compounds to determine which

is more suited "or )n*! even i" one o" the compounds is

secondary alkyl halide vs. the primary alkyl halide! i" the

backside attack o" the primary alkyl halide is hindered

then the )9%(<AR= alkyl halide is pre"erred

m. )tereochemistryi. 5nversion o" con>guration +think o" closed umbrella ?ying open

in wind,ii. %is to trans and vice versa! but i" cis&trans not applicable!

sometimes R&) are applicable but there is no guarantee that the

R&) con>gurations should change! draw the structure! the

important thing is that the structure has become inverted

n.



)n1o. )ubstitution! nucleophilic! unimolecular in rate determining step!

nucleophile does not play a role in rate determining step! solvolysis

solvent acts as the nucleophilep. 8ultistep process

i. irst step is a slow ioni6ation to "orm a carbocation! leavinggroup leaves

ii. )econd step is a "ast nucleophilic attack on the carbocation@. eak nucleophile usually used

i. 5" the nucleophile is an uncharged molecule then the positively

charged product must lose a proton to get >nal uncharged

product

r.s. %arbocation stability 30*010%H3/! also correlates to )n1 reactivityt. 5" nucleophile has multiple sites it can use to attack use the site that

will result in the most resonance stabili6ationu. :eaving group stability that o" )n*v. %arbocation resonance structures can make even secondary and

primary halides react as "ast as tertiary halides! you don$t necessarily

have to make a tertiary stabili6ed cation! and A:) allylic resonance

stabili6ation helpsw. )olvent eects ; polar protic solvents like alcohols and water are good

"or )n1! polar protic solvents solvate ions

x. )tereochemistry' racemi6ation occurs since the carbocation is planarand achiral! both enantiomers are "ormed +retention and inversion,!

normally the inversion product is "ormed in greater percentage since

the leaving group slightly hinders a "ront side attack! making a back

side attack more pre"erabley. %ARB%A-5( R9ARRA(G989(-)' done to create more stable

carbocations with hydride and methyl shi"ts! ring expansion is an

option too



)n1 vs )n*

91

6. 9limination involves the loss o" two atoms and the "ormation o" a pibondaa.)low step o" this reaction is the same as that o" )n1

ab.ac.(-9' the solvent acts as a base +to remove a hydrogen, rather than a

nucleophilead.587R-A(-' 91 and )n1 are %879-5-59 reactions! both happen

normallyae.%arbocation rearrangements occur! only the solvent acts as a base

instead o" a nucleophile! when comparing to )n1! don$t "orget ring

expansion as a possibility "or cyclobutane and below

a". %arbocation reactionsag.%yclopentane and cyclohexane are not very strained! so their

carbocations will open up only i" they have a dierent incentive! such

as going "rom secondary to tertiary cation.ah.#A5-)9$) RC:9' in elimination reactions! the most substituted alkene

predominates



ai.a2. Reactivity 30*001

9*ak.9limination! bimolecular! happens with strong BA)9)! note that strong

nucleophiles tend to be strong basesal. Reactivity' 30*01

am.an.9*&)n* compete in secondary alkyl halide reactionsao.#A5-)9$) RC:9 )-5:: A77:5%AB:9ap.)-9R9%H985)-R= 5) A77:5%AB:9' )=(%7:A(AR +DE, A(< A(-5

%7:A(AR +1FDE, arrangement o" halogen to hydrogen&alkyl group

necessary "or this reaction to occur! syncoplanar corresponds to

eclipsed con"ormation while anticoplanar corresponds to staggered

con"ormation! A:) anticoplanar corresponds to transdiaxial on

cyclohexane chairs

[email protected]. (-9' 5" you want 91 over )n1! use a strong acid R H5(<9R9< BA)9!

weak nucleophile! and heat! i" you want )n1 over 91 use an acid like

H%l! H5! HBr



91 and 9* summary

<ehydrohalogenation o" alkenes +"orm o" 91&9* reaction,+/55,as. H/ is lost "rom alkyl halide to give alkene! elimination reactionat. eak base needed "or 91 +91 competes with )n1,&)trong base "or 9*

au.

av.

5(A: (-9) ( %HA7-9R '1. -he strength o" the base or nucleophile determines the order o" the reaction.

*. 7rimary halides usually undergo the reaction! occasionally the 9* reaction

3. -ertiary halides usually undergo the 9* reaction +strong base, or a mixture o" )(1

and 91 +weak base,.

4. -he reactions o" secondary halides are the most dicult to predict.

I. )ome nucleophiles and bases "avor substitution or elimination



icinal dibromide elimination +R8 9*, o" alkenes

+/55,

aw.

Alcohol dehydration o" alcohols to "orm alkenes! "orm o"

elimination +/55,

ax.ay. Reactivity rate o" type o" alcohol' 30*01! 91

a6. )pecial case o" alcohol dehydration to "orm 9-H9R)



ba.

<ehydrogenation o" alkanes to "orm alkenes! elimination

+/55,

bb.

:ecture +/55, has some practice problems at the end! pg. 31 o" %hapter J has nice

problem solving strategy "or the reactions up to this point



G9(9RA: 89%HA(5)8 R 9:9%-R7H5:5% A<<5-5(

R9A%-5() A:K9(9)

+9lectrophilic, Additions o" H/ to alkenes

8ARK(5K$) rule comes into play! R9G5)9:9%-59

+/555,

bc.bd.L(- A )-9R9)9:9%-59 reaction because planar carbocation is

"ormed! the halogen can attack "rom either side "or syn or anti addition

resulting in cis&trans stereoisomers! see problem F1 "rom ade F th

edition "or detailsbe.)89 HBr addition is Antimarkovnical, only exception! it adds as a

radical due to light or peroxide presence! radical adds to the more

substituted carbon! stability o" radicals' 30*010radical %H3b". -he peroxide eect! which is reversal o" orientation in the presence o"

peroxide! occurs in HBr addition only! you get BOTH Markovnical and

Antimarkovnical products



bg.

bh.8arkovnikov$s rule states that carbocations are "ormed on the more

substituted carbon and that the addition o" H on one o" the carbons o"

the double bond will be on the carbon that least substituted

+9lectrophilic, Addition o" water&hydration +in a@ueous

acid solution, to "orm alkenes +/555,bi. 5llustrates principle o" microscopic reversibilitystates that whatever

process the "orward reaction took the reverse reaction must "ollow the

same reaction pathwayb2. Hydration involves the creation o" cations and cations 5::

R9ARRA(G9 - R8 8R9 )-AB:9 %A-5()

bk.

xymercuration&demercuration o" alkenes +electrophilic

addition A(< hydration, +/555,bl. A5<) 7RB:98 o" creating cations +unlike alcohol dehydration, and

"orms alcohols



bm. Markovnikov additionbn.Reagent is 8ercuric acetatebo.xymercuration involves an electrophilic attack on the double bond by

the positively charged mercury species. -he product is a mercurinium

ion! an organometallic cation containing a threemembered ringbp.5n the second step! water "rom the solvent attacks the mercurinium ion

to give +a"ter deprotonation, an organomercurial alcohol. A subse@uent

reaction is demercuration! to remove the mercury. )odium borohydride

+a reducing agent, replaces the mercuric acetate "ragment with a

hydrogen atom.

[email protected]. 5" this reaction is done in an alcohol it is alkoxymercuration

demercuration +convert alkenes to ethers,

i. hen mercuration takes place in an alcohol solvent! the alcoholserves as a nucleophile to attack the mercurinium ion. <RA

-H9 5( 5( -H9 89%HA(5)8. -he solvent attacks the

mercurinium ion at the more substituted end o" the double

bond +where there is more charge,! giving Markovnikov

orientation o" addition. -he Hg+Ac, group appears at the less

substituted end o" the double bond.

ii.

iii. Anti-addition occurs with this



iv.

Hydroboration o" alkenes +hydration reaction, +/555,bs.Csed to create antimarkovnikov alcohols "rom alkenes +less

substituted carbon o" the double bond is attacked by the H group,!

one step involving borane +BH3, acting as the electrophile attacking

the less substituted carbon o" the double bond! a "our membered

transition state is "ormed! then product o" this >rst step is "ormed with

retentions o" con>guration! then second step! oxidation occurs with

H** and a@ueous (aH' H "rom (aH attacks one o" thehydrogens on the peroxide to give (aH! which attacks the BH*!

"orces migration o" carbonboron bond onto the oxygenoxygen bond!

breaking it! and expelling an H group. -he H group comes back and

attaches to BH* to give BH*H! a good leaving group. -he le"t on

the carbon is then protonated by water or some acid.

bt.

bu.bv. Lsyn addition' on same side! both in "ront or behind plane!

stoichiometry' 3 alkenes "or 1 BH3 to "orm 3 alcoholsbw. 9nantiomers "orm +diastereomers, +racemi6ation,bx.LLLA:K9(9)-RA5(9< R5(G79(5(G



Additions o" halogens to alkenes! "orms vicinal dihalides

+electrophilic addition, +/555,

by.b6.ANTI-ADDITION! the electrophilic carbon double bond attacks the /*

+/*M%l* or Br*! sometimes 5*,! "orms three membered transition state

with one o" the /! and the other / anion is nucleophile attacking

backside to result in "ormation o" enantiomersca.)ome cases that can be true! but best to draw products out and check

i. 5" addition o" /* with a compound & cis or trans

transproduct +racemic,ii. 5" addition o" /* with compound & cis both enantiomers "ormiii. 5" addition o" /* with compound & transmesocompounds

"ormcb.LLLA:K9(9)-RA5(9< R5(G79(5(G

Halohydrin "ormation "rom alkenes+electrophilic addition,

+/5/,cc. Nust like addition o" halogens to alkenes! but instead o" having no

solvent&inert solvent! the solvent is nucleophilic! like water! so this

reaction is basically an addition o" halogens to alkenes in presence o"water&nucleophilic solvent.

cd.Markovnikovs rule! H attacks the more substituted carbon while

halide ion is attacked by the electrophilic double bond o" alkene! anti-

addition

ce.c". LLLA:K9(9)-RA5(9< R5(G79(5(G



%atalytic Hydrogenation o" alkenes ; +9lectrophilic

addition, +/555 O /5/,cg.!yn-addition o" hydrogens with 7t as solid heterogeneous catalystch.ne "ace o" the alkene pi bond binds to the catalyst! which has

hydrogen adsorbed on its sur"ace. Hydrogen inserts into the pi bond!

and the product is "reed "rom the catalyst. Both hydrogen atoms add to

the "ace o" the double bond that is complexed with the catalyst. -his is

heterogeneous catalysis since the catalyst is in a dierent phase "rom

the reactant solution.

ci.c2. Another +homogeneous, catalyst

ck.

9poxidation o" alkene to epoxide +electrophilic addition,

+/5/,cl. 5" you need to add oxygen to something use thisPPPcm. A peroxyacid +carboxylic acid with extra oxygen atom in an

bond! also highly selective oxidi6ing agent, converts an alkene to an

epoxide. A peroxyacid epoxidi6es an alkene by a concertedelectrophilic reaction where several bonds are broken and several are

"ormed at the same time. 9poxide retains stereochemistry o" starting

material.cn.m%7BA +mchloroperoxyben6oic acid, is the common solvent used! and

so is peroxyacetic acid +%H3%3H,

co.



[email protected] is then protonated by the acid and then a backside attack by

water opens the ring and the water attaches to the more substituted

carbon +8ARK(5K,! the end result is an A(-5A<<9< G:=%:

cr.cs. )ince this reaction is A(-5! there is a possibility "or certain isomers to

"orm based on the stereochemistry o" the starting material! see

halogenation o" alkenes "or details

ct. 8ight be extra in"o' 9poxidation reagents can be chosen to "avor eitherthe epoxide or the glycol. chiral diols. 7eroxyacetic acid is used in

strongly acidic water solutions. -he acidic solution protonates the

epoxide and converts it to the glycol. 7eroxyben6oic acids are weak

acids that can be used in nonnucleophilic solvents such as carbon

tetrachloride. m%hloroperoxyben6oic acid in generally gives good

yields o" epoxides. igure FF compares the uses o" these reagents.cu.LLLA:K9(9)-RA5(9< R5(G79(5(G

<ihydroxylation +* rxns! electrophilic addition, +)yn

hydroxylation special, o" alkenes to "orm glycols +/5/,cv. )CBR9A%-5(' smium tetroxide dihydroxylation! )=(A<<5-5( to

alkenes to give G:=%:! concerted +lots o" shi"ting happens at once like

with epoxidation, ester "ormedi. xidi6ing agents like peroxides and tertiary amine oxides used

to reoxidi6e osmium



ii.cw.)CBR9A%-5(' 7otassium permanganate dihydroxylation

i. Again! )=(A<<5-5( to give G:=%:! concerted ester "ormed

ii.cx.LLLA:K9(9)-RA5(9< R5(G79(5(G

xidative cleavage o" alkenes with 7otassium

permanganate +electrophilic addition, +/5/,cy. -his has the same initiation as 7otassium permanganate

dihydroxylation! only this time the potassium permanganate is

warm&concentrated. orms ketone compound and aldehyde compound!

the aldehyde compound is @uickly oxidi6ed into a carboxylic acid under

these conditions. 5" the molecule contains a terminal group! that group

is oxidi6ed all the way to % and water.

c6.

da.

6onolysisreduction o" alkenes +"orm o" oxidative

cleavage! all 2ust very complicated, +/5/,

db.)tep 1'



dc.)tep *' 8olo6onide is "ormed "rom the addition o" the o6one to the

double bond. 8olo6onide @uickly rearranges into o6onide. But even

that is unstable.dd.)tep 3' A reducing agent! like <imethyl sul>de is used to get >nal

products. (ote that <8) is "ormed +used in )(* reactionsP,.

de.-o predict the products "rom o6onolysis o" an alkene! erase the doublebond and add two oxygen atoms as carbonyl groups where the double

bond used to be. And to go backward given the products o" o6onolysis!

pretend like you$re about to smash the double bonded oxygens on

each product together +align them like you$re about to do that,! but

then erase the double bonded oxygens and "orm a double bond

between the carbons remaining.

d".

7olymeri6ation o" alkenes +/5/,dg.7rocess can be initiated by cations! radicals! anions

i. %ation is "ormed through protonation with some strong acid!then the polymer 2ust adds to itsel"! and at termination!

elimination occurs at the cation to give a terminal alkene as the



product. B3 is a good catalyst! section F1 ade.

ii. Radical polymeri6ation

iii. Anionic polymeri6ation

:ecture /5/ is the end o" alkenes ; acidbase reactions with alkenes occur with

(a(H* as the base! result in "ormation o" ammonia and some "orm o" an acetylenic

proton! this only happens with terminal alkynes.



Acetylide ormation

Acetylenic alcohols result when acetylides add to ketones

and aldehydes +)ection QJB,.". General reaction

#. A, Acetylide ion with "ormaldehyde primary alcohol$. B, Acetylide ion with aldehyde secondary alcohol%. %, Acetylide ion with keton tertiary alcohol

Hydrogenation o" alkynes +//5,

)CBR9A%-5(' %atalytic Hydrogenation to get cis Alkenesiv. :indlar$s catalystL is a poisoned palladium catalyst! composed o"

powdered barium sul"ate coated with palladium! poisoned with

@uinoline. )=(A<<5-5(. <oesn$t matter i" the alkyne is internal

or terminal.

v.

vi.

)CBR9A%-5(' 8etal&Ammonia Reduction to get trans Alkenesvii. A(-5A<<5-5(



viii.dh.(ote use o" hetero&homogenous catalysts

Addition o" halogens to alkynes +//5,

di.

Addition o" hydrogen halides +//5,d2. ery similar to this reaction with alkenesdk.8arkovnikov +his rule applies to only terminal alkynes, while

antimarkovnikov products "orm with radical HBrdl. (ote 9&# con>gurations



dm.dn.HBr addition in the presence o" a peroxide +radical! antimarkovnical,

do.

9nols are unstable species that can be turned into ketones and aldehydes through

acids or bases

Hydration o" alkynesgeneral +//5,8ercuric 5on %ataly6ed Hydration +8arkovnikov,

i.

ii.



acid cataly6ed ketoenol tautomerism

iii.

iv.

Base cataly6ed ketoenol tautomerism

v.

Hydroborationoxidation o" alkynes +enols! "orm o"

hydration, +//5,

dp.-urns alkynes into aldehydes! using R*BH in H**&(aH! A(-58ARK(5K addition



d@.

7ermanganate oxidation o" alkynes +//5,Cnder normal +cool&dilute conditions,

*. 5nternal alkyne results in diketone! while terminal alkyne results in a ketoacid

3.



arm concentrated +basic, conditions! note di b&w terminal&internal

6onolysis o" alkynes +"orm o" oxidative cleavage, +//5,

a.

)99 7G. 4I4 o" 7< +41 in book, "or 7RB:98 ):5(G )-RA-9G= R 8C:-5)-97

)=(-H9)5)P

:ecture //55 covers general in"ormation about alcoholsmight want to look at acidity

o" alcohols +7< 7G. 4J3! section 1D,



)ome alcohol synthesis'

)n*&)n1 on alkyl halide Acid cataly6ed hydration o" alkenes xymercurationdemercuration o" alkenes Hydroborationoxidation o" alkenes

)yndihydroxylation +s4!K8n4, and Antidihydroxylation +7eroxide inacid, o" alkenes +7< 7G. 4JF,

Addition o" acetylides to carbonyl compounds

:ecture //555 ; rganometallic reagents readily attack carbonyl compounds!

rganometallic compounds contain covalent bonds between carbon atoms and

metal atoms. rganometallic reagents are use"ul because they have nucleophilic

carbon atoms! in contrast to the electrophilic carbon atoms o" alkyl halides.

rganometallic reagent ; Grignard +//555,b. Grignard reaction speci>cs

i. Grignard addition to "ormaldehyde 0 primary alcohols +7<

pg.4F34F4,ii. Grignard addition to other aldehydes 0 secondary alcoholsiii. Grignard addition to ketones 0 tertiary alcohols

c.d. Grignard reagents cannot be made "rom any compounds with acidic

groups meaning H8g/ doesn$t exist

rganometallic reagent rganolithium reagent +//555,

e. -hese organometallic reagent reactions work with acyl chlorides!esters! and epoxides



".g. rganolithium reagents are more reactive than Grignard reagents

Grignard Reactions +//555,Grignard reaction! =C %A( C)9 -H5) - A<< 7R9--= 8C%H A(=

A(5(

i.

Grignard addition to acid chlorides and estersii. Grignard acid chloride +ether! H3, gives tertiary alcoholiii. Grignard ester +ether! H3, gives tertiary alcohol



iv.

Grignard addition to epoxides

v.

h.



)ide reactions o" organometallic compounds +//555,Reduction o" alkyl halides to alkanes

i.

i. Nust in case'

%arbonyl compound reduction to "orm alcohol +//555, 2. Cse o" :iAlH4 or (aBH4! :iAlH4 more reactive due to electronegativity

o" bonds! carbonyl group into alcohol! can synthesi6e primary and

secondary alcohols "rom this

k.



l.

-hiols can be prepared through )n* also

-hiol oxidation +//555,m. (ote creation o" disul>de bridge! thiols to disul>de

n.

-hiol exhaustive oxidation +//555,o. -hiols to sul"onic acids

p.



types

Alcohol xidation +//5,

@.

r.s. xidation o" secondary alcohols! ketone is product! (a*%r*J

+oxidi6ing agent, in H*)4! this is one possibility "or "orming a double

bond with oxygen to create only a carbonyl group without any

hydrogens attached to the carbon

t. xidation o" primary alcohols! initially "orms aldehyde which is @uickly

oxidi6ed to carboxylic acid



u.v. Csing 7%% as the oxidi6ing agent! the reaction can be stopped at the

aldehyde! and instead o" using something in H*! use an ether

w.x. -ertiary alcohols can$t be oxidi6ed +maybe use K8(4&H(3S,

Biological Alcohol xidation +//5,y. (A< is oxidi6ing agent

6.



ormation o" )ul"onate esters +//5,aa.Alcohols can act as nucleophiles and electrophiles

ab.How can we convert an alcohol to an electrophile that is compatiblewith basic nucleophilesS )ince H is bad leaving group! alcohols are

converted to tosylate esters. -osyl chloride and pyridine make up the

tosylate. 7yridine is a base which helps prevent side reactions.

ac.



Alcohol Reductions +//5,

ad.ae.Another path this could take is dehydration o" the alcohol and then use

hydrogenation o" alkene to give the >nal product

Reactions o" Alcohols with H/ +//5,a". %onvert alcohol into alkyl halide! protonation o" H group! then

nucleophilic attackag.7er"orms both )n1&)n*

ah.

ai.



Reactions o" Alcohols with 7hosphorus Halides +)n*,

a2.ak.Alcoholalkyl halideal. Reaction occurs normally with 7Br3 or the *7&35* combo +753,am. orks well with primary and secondary alcohols! kinda like )n*!

meaning no rearrangements occur

an.

Reactions o" Alcohols with )o%l* +thionyl chloride,ao.Good "or reactions with secondary and tertiary alcohols! has a special

mechanism similar to that o" )n1 in that it contains slow steps and a

carbocation is "ormed but the no rearrangements occur! leading to a

retention o" con>gurationap.Alcohol to alkyl halide

a@.

Reactions o" 7rimary Alcohols in acidic conditions +special

case o" dehydration o" alcohols,ar. Good "or reactions that involve primary alcohols! )n* type mechanism

in which the protonated alcohol may be attacked by another molecule

o" the alcohol



as. Csed industrially! is a "orm o" condensation +reaction that 2oins two or

more molecules! o"ten with loss o" small molecule like water,! this

R9A%-5( %879-9) 5-H 9:585(A-5(

at.

Cni@ue reactions o" diols7inacol Rearrangement

1. A "orm o" a dehydration reaction in acid cataly6ed conditions! results in extra

stability because a resonance stabili6ed carbocation is "ormed! deprotonation

o" carbocation give >nal product! which is pinacolone

*.

7eriodic Acid %leavage o" Glycols +alkenes&glycols to ketones and

aldehydes,1. ",#-Diols &'lycols(, suc) as t)ose *ormed by di)ydro+ylation o*

alkenes, are cleaved by periodic acid. T)e products are t)e same

ketones and alde)ydes that would be "ormed by o6onolysis;reduction o"the alkene. <ihydroxylation "ollowed by periodic acid cleavage serves as a

use"ul alternative to o6onolysis. %ycloalkenes go through an intermediate as

shown in the next to next bullet point.

*.



3.

4.

Alcohol reactions with carboxylic acids +ischer

9steri>cation,1. Alcohols react with carboxylic acids to "orm 9)-9R) +"orm o" condensation,

*.3. -he main problem with this reaction is that is reversible so acyl chlorides are

used to drive it "orward

4.

Alcohol Reactions with 5norganic acids1. Alcohols react with inorganic acids to "orm inorganic esters

)ul"ate 9sters

1.



(itrate 9sters

1.*. 9xamples +>rst two "rom le"t are (5-RB9(#9(9 derivatives! 79-( is nitrate

ester,'

7hosphate 9sters

1.



Reactions o" Alkoxides! metals w& alcoholos +illiamson

9ther )ynthesis! )n*,

1.

*.



Random -H5(G) you should know'

1. inyl halide ; halide attached to carbon in carboncarbon double bond +do

(- undergo )n1&*,*. Aryl halide +ben6ene ringsP, ; aromatic ring with halide substituent +do (-

undergo )n1&*,3. icinal halide ; halides attached to ad2acent carbons4. 9&# con>guration "or alkenes ; # is "or cis setup o" >rst priority groups on

carbons o" double bond! 9 is "or trans setup o" >rst priority groups on carbons

o" double bond! you have to use 9&# like R&)! so i" there are multiple double

bonds! make sure to indicate each bond with 9&#! A:A=) 75%K - A-8)( (95GHBR5(G %ARB() - )H %5)&-RA()! no geometric isomers

exist i" priority groups cannot be determined



I..

J. Regiochemistry also called the orientation o" addition! meaning which part

o" the reagent adds to which end o" the double bond! 587R-A(- 5(

9:9%-R7H5:5% A<<5-5() A:K9(9)F. -H5) 85GH- H9:7 5-H NC)- ABC- 99R=-H5(GPPP

Q.



1D.Know the dierence between terminal and internal alkynes

11.1*.A good @uestion

13.

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