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Reactions obviously covered in class

Radical Halogenation
a. Go back to 4.3 to review this reaction

Allylic Bromination
b. Allylic positions are those which are next to a carbon-carbon double
bond
c. Highly selective, only the most stable radical is formed through
resonance
d. Zaitsevs rule says that the most substituted product is the most stable
e. Common reagent/solvent: NBS

f.

Sn2
g. Nucleophilic substitution, bimolecular, one step, transition state exists,
in the transition state, a bond is partially formed with the nucleophile
(backside attack) and a bond is partially broken with the leaving group
(no intermediate), STRONG nucleophile needed
h. Reactivity: CH3X>1>2

i.

j.
k. Factors affecting Sn2:
i. Strength of nucleophile (secondary factor)
1. Trends in nucleophilicity
a. A species with a negative charge is a stronger
nucleophile than a similar neutral species. In
particular, a base is a stronger nucleophile than its
conjugate acid.
b. Nucleophilicity decreases from left to right in the
periodic table, following the increase in
electronegativity from left to right. The more
electronegative elements have more tightly held
nonbonding electrons that are less reactive toward
forming new bonds.

c. Nucleophilicity increases down the periodic table,


following the increase in size and polarizability, and
the decrease in electronegativity.
ii. Size and Polarizability (secondary factor)
1. More polarizable atoms/molecules are better for Sn2
iii. Steric hindrance (primary factor)
1. If we want a species to act as a base, we use a bulky
reagent like tert-butoxide ion (E2). If we want it to react as
a nucleophile, we use a less hindered reagent, like
ethoxide. Less branching, less steric hindrance.
iv. Solvent effects
1. POLAR PROTIC solvents acidic hydrogens (OH, NH
groups)
2. POLAR APROTIC solvents anions are not as solvated,
enhanced nucleophilicity, better for Sn2 (ex. Acetonitrile,
DMF, acetone)
l. Substrate factors in Sn2
i. Leaving Group effects on substrate
1. Good leaving groups must be electron withdrawing to
create partial positive/electrophilic carbon
2. Leaving group must be stable (weak bases, meaning
bases of strong acids)
3. Leaving group must be polarizable
ii. Steric hindrance of substrate
1. Note: when comparing to compounds to determine which
is more suited for Sn2, even if one of the compounds is
secondary alkyl halide vs. the primary alkyl halide, if the
backside attack of the primary alkyl halide is hindered
then the SECONDARY alkyl halide is preferred
m. Stereochemistry
i. Inversion of configuration (think of closed umbrella flying open
in wind)
ii. Cis to trans and vice versa, but if cis/trans not applicable,
sometimes R/S are applicable but there is no guarantee that the
R/S configurations should change, draw the structure, the
important thing is that the structure has become inverted

n.

Sn1
o. Substitution, nucleophilic, unimolecular in rate determining step,
nucleophile does not play a role in rate determining step, solvolysissolvent acts as the nucleophile
p. Multistep process
i. First step is a slow ionization to form a carbocation, leaving
group leaves
ii. Second step is a fast nucleophilic attack on the carbocation
q. Weak nucleophile usually used
i. If the nucleophile is an uncharged molecule then the positively
charged product must lose a proton to get final uncharged
product

r.
s. Carbocation stability 3>2>1>CH3X, also correlates to Sn1 reactivity
t. If nucleophile has multiple sites it can use to attack use the site that
will result in the most resonance stabilization
u. Leaving group stability that of Sn2
v. Carbocation resonance structures can make even secondary and
primary halides react as fast as tertiary halides, you dont necessarily
have to make a tertiary stabilized cation, and ALSO allylic resonance
stabilization helps
w. Solvent effects polar protic solvents like alcohols and water are good
for Sn1, polar protic solvents solvate ions
x. Stereochemistry: racemization occurs since the carbocation is planar
and achiral, both enantiomers are formed (retention and inversion),
normally the inversion product is formed in greater percentage since
the leaving group slightly hinders a front side attack, making a back
side attack more preferable
y. CARBOCATION REARRANGEMENTS: done to create more stable
carbocations with hydride and methyl shifts, ring expansion is an
option too

Sn1 vs Sn2

E1
z. Elimination involves the loss of two atoms and the formation of a pi
bond
aa.Slow step of this reaction is the same as that of Sn1

ab.
ac. NOTE: the solvent acts as a base (to remove a hydrogen) rather than a
nucleophile
ad.IMPORTANT: E1 and Sn1 are COMPETITIVE reactions, both happen
normally
ae.Carbocation rearrangements occur, only the solvent acts as a base
instead of a nucleophile, when comparing to Sn1, dont forget ring
expansion as a possibility for cyclobutane and below

af. Carbocation reactions


ag.Cyclopentane and cyclohexane are not very strained, so their
carbocations will open up only if they have a different incentive, such
as going from secondary to tertiary cation.
ah.ZAITSEVS RULE: in elimination reactions, the most substituted alkene
predominates

ai.
aj. Reactivity 3>2>>1

E2
ak. Elimination, bimolecular, happens with strong BASES, note that strong
nucleophiles tend to be strong bases
al. Reactivity: 3>2>1

am.
an.E2/Sn2 compete in secondary alkyl halide reactions
ao. ZAITSEVS RULE STILL APPLICABLE
ap.STEREOCHEMISTRY IS APPLICABLE: SYN-COPLANAR (0) AND ANTICOPLANAR (180) arrangement of halogen to hydrogen/alkyl group
necessary for this reaction to occur, syn-coplanar corresponds to
eclipsed conformation while anti-coplanar corresponds to staggered
conformation, ALSO anti-coplanar corresponds to trans-diaxial on
cyclohexane chairs

aq.
ar. NOTE: If you want E1 over Sn1, use a strong acid OR HINDERED BASE,
weak nucleophile, and heat, if you want Sn1 over E1 use an acid like
HCl, HI, HBr

E1 and E2 summary

Dehydrohalogenation of alkenes (form of E1/E2 reaction)


(XVII)
as. H-X is lost from alkyl halide to give alkene, elimination reaction
at. Weak base needed for E1 (E1 competes with Sn1)/Strong base for E2

au.

av.

FINAL NOTES ON CHAPTER 6:


1. The strength of the base or nucleophile determines the order of the reaction.
2. Primary halides usually undergo the reaction, occasionally the E2 reaction
3. Tertiary halides usually undergo the E2 reaction (strong base) or a mixture of SN1
and E1 (weak base).
4. The reactions of secondary halides are the most difficult to predict.
5. Some nucleophiles and bases favor substitution or elimination

Vicinal dibromide elimination (FORM OF E2) of alkenes


(XVII)

aw.

Alcohol dehydration of alcohols to form alkenes, form of


elimination (XVII)

ax.
ay. Reactivity rate of type of alcohol: 3>2>1, E1
az. Special case of alcohol dehydration to form ETHERS

ba.

Dehydrogenation of alkanes to form alkenes, elimination


(XVII)

bb.
Lecture (XVII) has some practice problems at the end, pg. 316 of Chapter 7 has nice
problem solving strategy for the reactions up to this point

GENERAL MECHANISM FOR ELECTROPHILIC ADDITION


REACTIONS OF ALKENES

(Electrophilic) Additions of HX to alkenes MARKOVNIKOVS rule comes into play, REGIOSELECTIVE


(XVIII)

bc.
bd.*NOT A STEREOSELECTIVE reaction because planar carbocation is
formed, the halogen can attack from either side for syn or anti addition
resulting in cis/trans stereoisomers, see problem 8-16 from Wade 8 th
edition for details
be.SOME 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 of radicals: 3>2>1>radical CH3
bf. The peroxide effect, which is reversal of orientation in the presence of
peroxide, occurs in HBr addition only, you get BOTH Markovnical and
Antimarkovnical products

bg.

bh.Markovnikovs rule states that carbocations are formed on the more


substituted carbon and that the addition of H on one of the carbons of
the double bond will be on the carbon that least substituted

(Electrophilic) Addition of water/hydration (in aqueous


acid solution) to form alkenes (XVIII)
bi. Illustrates principle of microscopic reversibility-states that whatever
process the forward reaction took the reverse reaction must follow the
same reaction pathway
bj. Hydration involves the creation of cations and cations WILL
REARRANGE TO FORM MORE STABLE CATIONS

bk.

Oxymercuration/demercuration of alkenes (electrophilic


addition AND hydration) (XVIII)
bl. AVOIDS PROBLEM of creating cations (unlike alcohol dehydration) and
forms alcohols

bm.
Markovnikov addition
bn.Reagent is Mercuric acetate
bo.Oxymercuration involves an electrophilic attack on the double bond by
the positively charged mercury species. The product is a mercurinium
ion, an organometallic cation containing a three-membered ring
bp.In the second step, water from the solvent attacks the mercurinium ion
to give (after deprotonation) an organomercurial alcohol. A subsequent
reaction is demercuration, to remove the mercury. Sodium borohydride
(a reducing agent) replaces the mercuric acetate fragment with a
hydrogen atom.

bq.
br. If this reaction is done in an alcohol it is alkoxymercurationdemercuration (convert alkenes to ethers)
i. When mercuration takes place in an alcohol solvent, the alcohol
serves as a nucleophile to attack the mercurinium ion. DRAW
THE ION IN THE MECHANISM. The solvent attacks the
mercurinium ion at the more substituted end of the double
bond (where there is more charge), giving Markovnikov
orientation of addition. The Hg(OAc) group appears at the less
substituted end of the double bond.

ii.
iii. Anti-addition occurs with this

iv.

Hydroboration of alkenes (hydration reaction) (XVIII)


bs. Used to create antimarkovnikov alcohols from alkenes (less
substituted carbon of the double bond is attacked by the OH group),
one step involving borane (BH3) acting as the electrophile attacking
the less substituted carbon of the double bond, a four membered
transition state is formed, then product of this first step is formed with
retentions of configuration, then second step, oxidation occurs with
H2O2 and aqueous NaOH: OH- from NaOH attacks one of the
hydrogens on the peroxide to give NaOOH, which attacks the BH2,
forces migration of carbon-boron bond onto the oxygen-oxygen bond,
breaking it, and expelling an OH group. The OH group comes back and
attaches to BH2 to give BH2OH, a good leaving group. The O- left on
the carbon is then protonated by water or some acid.

bt.

bu.
bv. *syn addition: on same side, both in front or behind plane,
stoichiometry: 3 alkenes for 1 BH3 to form 3 alcohols
bw.
Enantiomers form (diastereomers) (racemization)
bx.***ALKENESTRAINED RINGOPENING

Additions of halogens to alkenes, forms vicinal dihalides


(electrophilic addition) (XVIII)

by.
bz. ANTI-ADDITION, the electrophilic carbon double bond attacks the X2
(X2=Cl2 or Br2, sometimes I2), forms three membered transition state
with one of the X, and the other X anion is nucleophile attacking
backside to result in formation of enantiomers
ca. Some cases that can be true, but best to draw products out and check
i. If addition of X2 with a compound W/O cis or transtrans
product (racemic)
ii. If addition of X2 with compound W/ cis both enantiomers form
iii. If addition of X2 with compound W/ transmeso-compounds
form
cb. ***ALKENESTRAINED RINGOPENING

Halohydrin formation from alkenes(electrophilic addition)


(XIX)
cc. Just like addition of halogens to alkenes, but instead of having no
solvent/inert solvent, the solvent is nucleophilic, like water, so this
reaction is basically an addition of halogens to alkenes in presence of
water/nucleophilic solvent.
cd. Markovnikovs rule, OH attacks the more substituted carbon while
halide ion is attacked by the electrophilic double bond of alkene, antiaddition

ce.
cf. ***ALKENESTRAINED RINGOPENING

Catalytic Hydrogenation of alkenes (Electrophilic


addition) (XVIII & XIX)
cg. Syn-addition of hydrogens with Pt as solid heterogeneous catalyst
ch. One face of the alkene pi bond binds to the catalyst, which has
hydrogen adsorbed on its surface. Hydrogen inserts into the pi bond,
and the product is freed from the catalyst. Both hydrogen atoms add to
the face of the double bond that is complexed with the catalyst. This is
heterogeneous catalysis since the catalyst is in a different phase from
the reactant solution.

ci.
cj. Another (homogeneous) catalyst

ck.

Epoxidation of alkene to epoxide (electrophilic addition)


(XIX)
cl. If you need to add oxygen to something use this!!!
cm.
A peroxyacid (carboxylic acid with extra oxygen atom in an O-O
bond, also highly selective oxidizing agent) converts an alkene to an
epoxide. A peroxyacid epoxidizes an alkene by a concerted
electrophilic reaction where several bonds are broken and several are
formed at the same time. Epoxide retains stereochemistry of starting
material.
cn. mCPBA (m-chloroperoxybenzoic acid) is the common solvent used, and
so is peroxyacetic acid (CH3CO3H)

co.

cp.
cq. Epoxide 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 (MARKOVNIKOV), the end result is an ANTI-ADDED GLYCOL

cr.
cs. Since this reaction is ANTI, there is a possibility for certain isomers to
form based on the stereochemistry of the starting material, see
halogenation of alkenes for details
ct. Might be extra info: Epoxidation reagents can be chosen to favor either
the epoxide or the glycol. chiral diols. Peroxyacetic acid is used in
strongly acidic water solutions. The acidic solution protonates the
epoxide and converts it to the glycol. Peroxybenzoic acids are weak
acids that can be used in nonnucleophilic solvents such as carbon
tetrachloride. m-Chloroperoxybenzoic acid in generally gives good
yields of epoxides. Figure 8-8 compares the uses of these reagents.
cu. ***ALKENESTRAINED RINGOPENING

Dihydroxylation (2 rxns, electrophilic addition) (Synhydroxylation - special) of alkenes to form glycols (XIX)
cv. SUB-REACTION: Osmium tetroxide dihydroxylation, SYN-ADDITION to
alkenes to give GLYCOL, concerted (lots of shifting happens at once like
with epoxidation) ester formed
i. Oxidizing agents like peroxides and tertiary amine oxides used
to reoxidize osmium

ii.
cw.SUB-REACTION: Potassium permanganate dihydroxylation
i. Again, SYN-ADDITION to give GLYCOL, concerted ester formed

ii.
cx. ***ALKENESTRAINED RINGOPENING

Oxidative cleavage of alkenes with Potassium


permanganate (electrophilic addition) (XIX)
cy. This has the same initiation as Potassium permanganate
dihydroxylation, only this time the potassium permanganate is
warm/concentrated. Forms ketone compound and aldehyde compound,
the aldehyde compound is quickly oxidized into a carboxylic acid under
these conditions. If the molecule contains a terminal group, that group
is oxidized all the way to CO and water.

cz.

da.

Ozonolysis-reduction of alkenes (form of oxidative


cleavage, all just very complicated) (XIX)
db.Step 1:

dc. Step 2: Molozonide is formed from the addition of the ozone to the
double bond. Molozonide quickly rearranges into ozonide. But even

that is unstable.
dd.Step 3: A reducing agent, like Dimethyl sulfide is used to get final
products. Note that DMSO is formed (used in SN2 reactions!).

de.To predict the products from ozonolysis of an alkene, erase the double
bond and add two oxygen atoms as carbonyl groups where the double
bond used to be. And to go backward given the products of ozonolysis,
pretend like youre about to smash the double bonded oxygens on
each product together (align them like youre about to do that), but
then erase the double bonded oxygens and form a double bond
between the carbons remaining.

df.

Polymerization of alkenes (XIX)


dg.Process can be initiated by cations, radicals, anions
i. Cation is formed through protonation with some strong acid,
then the polymer just adds to itself, and at termination,
elimination occurs at the cation to give a terminal alkene as the

product. BF3 is a good catalyst, section 8-16 Wade.

ii. Radical polymerization

iii. Anionic polymerization

Lecture XIX is the end of alkenes acid-base reactions with alkenes occur with
NaNH2 as the base, result in formation of ammonia and some form of an acetylenic
proton, this only happens with terminal alkynes.

Acetylide Formation

Acetylenic alcohols result when acetylides add to ketones


and aldehydes (Section 9-7B).
1. General reaction

2. A) Acetylide ion with formaldehyde primary alcohol


3. B) Acetylide ion with aldehyde secondary alcohol
4. C) Acetylide ion with keton tertiary alcohol

Hydrogenation of alkynes (XXI)


SUB-REACTION: Catalytic Hydrogenation to get cis Alkenes
iv. Lindlars catalyst* is a poisoned palladium catalyst, composed of
powdered barium sulfate coated with palladium, poisoned with
quinoline. SYN-ADDITION. Doesnt matter if the alkyne is internal
or terminal.

v.

vi.

SUB-REACTION: Metal/Ammonia Reduction to get trans Alkenes


vii. ANTI-ADDITION

viii.
dh.Note use of hetero/homogenous catalysts

Addition of halogens to alkynes (XXI)

di.

Addition of hydrogen halides (XXI)


dj. Very similar to this reaction with alkenes
dk. Markovnikov (his rule applies to only terminal alkynes) while
antimarkovnikov products form with radical HBr
dl. Note E/Z configurations

dm.
dn.HBr addition in the presence of a peroxide (radical, antimarkovnical)

do.
Enols are unstable species that can be turned into ketones and aldehydes through
acids or bases

Hydration of alkynes-general (XXI)


Mercuric Ion Catalyzed Hydration (Markovnikov)

i.

ii.

acid catalyzed keto-enol tautomerism

iii.

iv.

Base catalyzed keto-enol tautomerism

v.

Hydroboration-oxidation of alkynes (enols, form of


hydration) (XXI)
dp.Turns alkynes into aldehydes, using R2BH in H2O2/NaOH, ANTIMARKOVNIKOV addition

dq.

Permanganate oxidation of alkynes (XXI)


Under normal (cool/dilute conditions)
2. Internal alkyne results in diketone, while terminal alkyne results in a keto-acid

3.

Warm concentrated (basic) conditions, note diff b/w terminal/internal

Ozonolysis of alkynes (form of oxidative cleavage) (XXI)

a.
SEE PG. 454 of PDF (416 in book) for PROBLEM SOLVING STRATEGY FOR MULTISTEP
SYNTHESIS!
Lecture XXII covers general information about alcohols-might want to look at acidity
of alcohols (PDF PG. 473, section 10-6)

Some alcohol synthesis:


-

Sn2/Sn1 on alkyl halide


Acid catalyzed hydration of alkenes
Oxymercuration-demercuration of alkenes
Hydroboration-oxidation of alkenes
Syn-dihydroxylation (OsO4,KMnO4) and Anti-dihydroxylation (Peroxide in
acid) of alkenes (PDF PG. 478)
Addition of acetylides to carbonyl compounds

Lecture XXIII Organometallic reagents readily attack carbonyl compounds,


Organometallic compounds contain covalent bonds between carbon atoms and
metal atoms. Organometallic reagents are useful because they have nucleophilic
carbon atoms, in contrast to the electrophilic carbon atoms of alkyl halides.

Organometallic reagent Grignard (XXIII)


b. Grignard reaction specifics
i. Grignard addition to formaldehyde -> primary alcohols (PDF
pg.483-484)
ii. Grignard addition to other aldehydes -> secondary alcohols
iii. Grignard addition to ketones -> tertiary alcohols

c.
d. Grignard reagents cannot be made from any compounds with acidic
groups meaning HMgX doesnt exist

Organometallic reagent - Organolithium reagent (XXIII)


e. These organometallic reagent reactions work with acyl chlorides,
esters, and epoxides

f.
g. Organolithium reagents are more reactive than Grignard reagents

Grignard Reactions (XXIII)


Grignard reaction, YOU CAN USE THIS TO ADD PRETTY MUCH ANY
ANION

i.

Grignard addition to acid chlorides and esters


ii. Grignard + acid chloride (ether, H3O+) gives tertiary alcohol
iii. Grignard + ester (ether, H3O+) gives tertiary alcohol

iv.

Grignard addition to epoxides

v.

h.

Side reactions of organometallic compounds (XXIII)


Reduction of alkyl halides to alkanes

i.

i.

Just in case:

Carbonyl compound reduction to form alcohol (XXIII)


j.

k.

Use of LiAlH4 or NaBH4, LiAlH4 more reactive due to electronegativity


of bonds, carbonyl group into alcohol, can synthesize primary and
secondary alcohols from this

l.
Thiols can be prepared through Sn2 also

Thiol oxidation (XXIII)


m. Note creation of disulfide bridge, thiols to disulfide

n.

Thiol exhaustive oxidation (XXIII)


o. Thiols to sulfonic acids

p.

types
Alcohol Oxidation (XXIV)
q.

r.
s. Oxidation of secondary alcohols, ketone is product, Na2Cr2O7
(oxidizing agent) in H2SO4, this is one possibility for forming a double
bond with oxygen to create only a carbonyl group without any
hydrogens attached to the carbon

t. Oxidation of primary alcohols, initially forms aldehyde which is quickly


oxidized to carboxylic acid

u.
v. Using PCC as the oxidizing agent, the reaction can be stopped at the
aldehyde, and instead of using something in H2O, use an ether

w.
x. Tertiary alcohols cant be oxidized (maybe use KMNO4/HNO3?)

Biological Alcohol Oxidation (XXIV)


y. NAD+ is oxidizing agent

z.

Formation of Sulfonate esters (XXIV)


aa.Alcohols can act as nucleophiles and electrophiles

ab.How can we convert an alcohol to an electrophile that is compatible


with basic nucleophiles? Since OH is bad leaving group, alcohols are
converted to tosylate esters. Tosyl chloride and pyridine make up the
tosylate. Pyridine is a base which helps prevent side reactions.

ac.

Alcohol Reductions (XXIV)

ad.
ae.Another path this could take is dehydration of the alcohol and then use
hydrogenation of alkene to give the final product

Reactions of Alcohols with HX (XXIV)


af. Convert alcohol into alkyl halide, protonation of OH group, then
nucleophilic attack
ag.Performs both Sn1/Sn2

ah.

ai.

Reactions of Alcohols with Phosphorus Halides (Sn2)

aj.
ak. Alcoholalkyl halide
al. Reaction occurs normally with PBr3 or the 2P/3I2 combo (PI3)
am.
Works well with primary and secondary alcohols, kinda like Sn2,
meaning no rearrangements occur

an.

Reactions of Alcohols with SoCl2 (thionyl chloride)


ao. Good for reactions with secondary and tertiary alcohols, has a special
mechanism similar to that of Sn1 in that it contains slow steps and a
carbocation is formed but the no rearrangements occur, leading to a
retention of configuration
ap.Alcohol to alkyl halide

aq.

Reactions of Primary Alcohols in acidic conditions (special


case of dehydration of alcohols)
ar. Good for reactions that involve primary alcohols, Sn2 type mechanism
in which the protonated alcohol may be attacked by another molecule
of the alcohol

as. Used industrially, is a form of condensation (reaction that joins two or


more molecules, often with loss of small molecule like water), this
REACTION COMPETES WITH ELIMINATION

at.

Unique reactions of diols


Pinacol Rearrangement
1. A form of a dehydration reaction in acid catalyzed conditions, results in extra
stability because a resonance stabilized carbocation is formed, deprotonation
of carbocation give final product, which is pinacolone

2.

Periodic Acid Cleavage of Glycols (alkenes/glycols to ketones and


aldehydes)
1. 1,2-Diols (glycols), such as those formed by dihydroxylation of
alkenes, are cleaved by periodic acid. The products are the same
ketones and aldehydes that would be formed by ozonolysisreduction of
the alkene. Dihydroxylation followed by periodic acid cleavage serves as a
useful alternative to ozonolysis. Cycloalkenes go through an intermediate as
shown in the next to next bullet point.

2.

3.

4.

Alcohol reactions with carboxylic acids (Fischer


Esterification)
1. Alcohols react with carboxylic acids to form ESTERS (form of condensation)

2.
3. The main problem with this reaction is that is reversible so acyl chlorides are
used to drive it forward

4.

Alcohol Reactions with Inorganic acids


1. Alcohols react with inorganic acids to form inorganic esters

Sulfate Esters

1.

Nitrate Esters

1.
2. Examples (first two from left are NITROBENZENE derivatives, PETN is nitrate

ester):

Phosphate Esters

1.

Reactions of Alkoxides, metals w/ alcoholos (Williamson


Ether Synthesis, Sn2)

1.

2.

Random THINGS you should know:


1. Vinyl halide halide attached to carbon in carbon-carbon double bond (do
NOT undergo Sn1/2)
2. Aryl halide (benzene rings!) aromatic ring with halide substituent (do NOT
undergo Sn1/2)
3. Vicinal halide halides attached to adjacent carbons
4. E/Z configuration for alkenes Z is for cis setup of first priority groups on
carbons of double bond, E is for trans setup of first priority groups on carbons
of double bond, you have to use E/Z like R/S, so if there are multiple double
bonds, make sure to indicate each bond with E/Z, ALWAYS PICK TWO ATOMS
ON NEIGHBORING CARBONS TO SHOW CIS/TRANS, no geometric isomers
exist if priority groups cannot be determined

5.
6.

7. Regiochemistry - also called the orientation of addition, meaning which part


of the reagent adds to which end of the double bond, IMPORTANT IN
ELECTROPHILIC ADDITIONS OF ALKENES
8. THIS MIGHT HELP WITH JUST ABOUT EVERYTHING!!!

9.

10.Know the difference between terminal and internal alkynes

11.
12.A good question

13.