Organic Chemistry 2 Final, Reagents and Reactions
Overall Reactivity of Carbonyl Groups
Acyl Chloride > acid anhydride > aldehyde > ketone > ester = carboxylic acid > amide
aldehyde plus Grignard forms a
secondary alcohol
When a carbon is bonded to 2 hydrogen and 2 non-identical groups
enantiotopic (1 signal)
When a carbon is bonded to 2 hydrogens in a compound with an asymmetric center
diastereotopic (2 signals)
(2C + 2 – #H – #X + #N)/2
Formula for degree of unsaturations
rings and double bonds count for how may degrees of unsaturation?
1 – One
Triple bonds count for how many degrees of unsaturation
2 – Two
What are the steps to determining NMR spectrum
1) Determine degree of unsaturation
2) Look of rings at 6.5 – 8.0
– Number of sub. = 6 – #aromatic protons
3) Look for aldehydes (sharp singlet past 9)
Look for alcohols (broad anywhere)
4) Add up integration and match to formula
5) Start putting the pieces together
2) Look of rings at 6.5 – 8.0
– Number of sub. = 6 – #aromatic protons
3) Look for aldehydes (sharp singlet past 9)
Look for alcohols (broad anywhere)
4) Add up integration and match to formula
5) Start putting the pieces together
Nucleophiles act by donating a pair of ________________________ or its electron _________________________.
electrons, density
Formaldehyde + Grignard
primary alcohol
Ketone + Grignard
tertiary alcohol
When an organometallic performs ring opening, it attacks the __________________ substituted side.
less
What are the three main oxidizing agents
1) Chromic Acid (H2CrO4) – Na2Cr2O7 / H2SO4
2) PCC / Ch2Cl2
3) NaOCl / Ch3COOH
2) PCC / Ch2Cl2
3) NaOCl / Ch3COOH
Chromic Acid will oxidize a secondary alcohol to a __________________.
Ketone
Chromic Acid will oxidize a primary alcohol to an __________________ and then to a ______________________.
aldehyde, carboxylic acid
PCC will oxidize a primary alcohol to an _____________________.
aldehyde
To oxidize a primary alcohol to an aldehyde, use ___________.
PCC
To oxidize a primary alcohol to carboxylic acid, use _________________.
Chromic Acid
Terminal alkyne + strong base (NaNH2) = _____________________
acetylide ion
Acetylide + aldehyde/ketone + weak acid (pyridine) = __________________
alcohol with triple bond
Reaction of cyanide with an aldehyde/ketone = ___________________
cyanohydrin (alcohol with C triple bond N)
Acid catalyzed hydrolysis of cyanohydrin produces an _____________________________.
alpha carboxylic acid
What are the two main hydrides used in reduction reactions
Lithium aluminum hydride and sodium borohydride
Which hydride is used to reduce aldehydes and ketones
sodium borohydride
sodium borohydride reduces aldehydes to _________________ and ketones to __________________.
primary alcohols, secondary alcohols
What is required following the reaction of an aldehyde or ketone with a hydride?
acid work-up to protonate and create the alcohol
Catalytic addition of hydrogen with H2 to a cyanohydrin forms a ________________________.
primary amine
What is the best way to make a terminal alkene
Wittig Reaction
The Wittig reaction involved the reaction of an aldehyde or ketone with a _______________ _______________.
phosphonium ylide
The Wittig reaction replaces the carbon oxygen double bond with a _______________, ________________ double bond.
carbon carbon
Addition of water to an aldehyde or ketone, produces a ______________.
Hydrate
What is a hydrate and what reagents are need to form it.
Molecule with two -OH groups bonded to the same carbon.
H2O and Acid – acid catalyzed
Acid Catalyzed reaction of aldehydes and ketones with alcohols forms a ____________________ after one addition and a ________________ after the second addition.
hemiacetal, acetal
Using a 1,2-diol as a protecting group forms a ___________ membered ring and the use of 1,3-diol forms a ___________ membered ring.
five, six
Reaction of aldehydes and ketones with a primary amine and trace acid produces an ___________________.
Imine
In the formation of an imine, the carbon, oxygen double bond is replaced by a __________________, ____________________double bond.
carbon, nitrogen
What reagents required for the synthesis of imine?
1) aldehyde / ketone
2) primary amine (RNH2)
3) trace acid
2) primary amine (RNH2)
3) trace acid
An enamine is a ________________ amine with a ______________ bond in the alpha, beta position relative to the nitrogen.
tertiary, double
In the formation of an enamine…After reacting an aldehyde or ketone with a secondary amine, ________________ is eliminated forming the tertiary amine.
water
Integrated values on an NMR are reported in the _______________ form.
reduced
The peak intensity changes/remains constant in a double of doublets.
remains constant
What determines the reactivity of organometallics?
The electronegativity of the metal. The more electronegative, the more reactive
Why are organolithiums more reactive than organocuprates?
The Organolithium bond is more polar than the organocuprate bond.
When determining the number of signals in a compound with cyclohexane, keep in mind that the ring can _____________.
ring flip
Which reducing agent is used to reduce carboxylic acids and esters
Lithium aluminum hydride
What determines the ease in preparation of ylides?
sterics and degree of substitution.
When an ylide reacts with an aldehyde or ketone, the P-C bond is ________________ and a ______________ double bond forms between the ______________ carbon and the carbon from the ylide.
broken, new, carbonyl
How do you determine if hydrogens are homotopic. enantiotopic. or diastereotopic?
Deuterium substitution
Propanoic Acid
Propanoyl Chloride
Phenyl Propanoate
Steps for naming esters
1) R group attached to carboxylic oxygen named first
2) followed by name of acid with “ic acid” replaced by “ate”
2) followed by name of acid with “ic acid” replaced by “ate”
ethyl ethanoate
___________________ agents convert alcohols to carbonyls
oxidizing
PCC oxidizes primary alcohols to ___________________ and secondary alcohols to ________________?
aldehydes, ketones
Chromic acid oxidizes secondary alcohols to _______________ and primary alcohols to ____________________?
ketones, carboxylic acids
Wittig reactions form terminal __________________.
alkenes
Retrosynthetic analysis of Wittig reagents favor the ________________ substituted alkyl halide.
less
When a Grignard reacts with CO2, __________________ is produced.
a carboxylic acid
Strong base add _____________________ without the aid of an ___________________ catalyst.
irreversibly, acid
What are the strong bases
1) Grignards
2) Organolithium
3) Hydrides
4) Wittig
2) Organolithium
3) Hydrides
4) Wittig
When strong bases add to carbonyl carbons, they add 1,___ and acid is added in a ________________ step.
2, separate
Weaker bases require the assistance of an acid _______________.
catalyst
Reactivity within aldehydes and ketones is reliant on….
Substituents. (Both hydrogen is most reactive, 2 large bulky substituents are least reactive)
If a carbonyl is in the presence of acid, the oxygen acts as a ________________ base and is more _______________.
Lewis, electrophilic
The addition of an acid catalyst increases the ________________ of the reaction only.
rate
Why is hydrate formation reversible?
Water and alcohols are weaker nucleophiles
What conditions are required for hydrate formation and why?
acidic to increase the electrophilicity of the carbonyl carbon
Protecting groups, protect ___________________ carbons from reactions that they otherwise would not survive.
carbonyl
Grignards in the presence of an _______________ proton, will quench!
acidic
When a nucleophile attacks an sp2 carbon, ______________ products can form.
multiple/2
Hydrate Mechanism
Conjugate addition is known as the _____________ product.
thermodynamic
Direct addition is known as the _____________ product.
kinetic
Enamines are similar to ___________, except that the carbonyl oxygen is replaced with NR2.
enolates
The formation of enamines is _________________ catalyzed.
acid
Enamine Mechanism
Why is water/acid added stepwise with grignards?
Quench
What reagents make up pyridine chlorochromate
What conditions are necessary when using PCC and why
anhydrous to prevent further oxidation
Bleach oxidation turns secondary alcohols to ___________________ and primary alcohols to ___________________.
ketones, aldehydes
In the reduction reaction with hydrides, the nucleophile is the _________________.
hydride ion (H)
In a phosphonium ylide, the majority of electron density resides on which atom?
carbon
Wittig reactions are preferred for making ___________________ alkenes.
terminal
Alpha hydrogens are more acidic because the conjugate ________________ is more stable through _____________.
base, resonance
Aldehydes an ketones are more acidic because in an ester, two pairs of protons __________________ for delocalization.
compete
LDA will convert ________________ of a carbonyl compound to enolate ions.
ALL
Halogenation of the alpha carbon uses what reagents?
X2 and acid
Halogenation can be _________________ catalyzed or _________________ promoted.
acid, base
In a base promoted halogenation, the base removes an alpha proton and _______________ alpha protons are replaced by the halogen.
ALL
In an acid catalyzed halogenation, ______________ alpha proton is replaced.
One
In a base promoted halogenation, the _______________ attacks the electrophilic halogen.
enolate
Alpha carbon alkylation requires the removal of an alpha carbon with _______________.
LDA
____________________is the required solvent for LDA.
THF
The kinetic alkylation product is formed _________________ and uses LDA at -78.
faster
The thermodynamic alkylation product can be formed using 0.95% _________________ and 0.05% __________________.
LDA, NaOH
In an aldol addition, the alpha carbon of one aldehyde/ketone acts as the ________________, and attacks the ________________ carbon of another.
nucleophile, carbonyl
The first step of an aldol addition is the removal of an alpha proton with a ________________.
base
An alcohol in the 3 position indicates a _________________ addition.
aldol
Dehydration of aldol addition forms _____________________________- aldehydes and ketones
alpha, beta unsaturated
Aldol condensation requires
heat and acid, or base and heat
The basic mechanism for aldol condensation begins with the base removing an alpha proton.
In a crossed aldol, one of the reactants must have no _________________ protons.
alpha
Aside from using one reactant without alpha protons, you can use _____________ and add the other slowly.
LDA
To determine the starting material of an aldol addition, locate the new ___________-____________ bond (formed with the alpha carbon, and draw the two reactants.
carbon carbon
To determine the starting material of an aldol condensation, convert the _____________-______________ unsaturated carbonyl to a _________________-hydroycarbonyl.
alpha, beta, beta
When two ester molecules undergo condensation, the process is called a ____________ condensation.
Claisen
The base used in a Claisen condensation is the same as the _________________________.
leaving group
Claisen Condensation versus Aldol addition products.
Carboxylic acids with a carbonyl group at the 3 position will undergo _________________________ in the presence of acid and heat.
decarboxylation
Decarboxylation is easier under ______________ conditions
acidic
The malonic ester synthesis combines the _______________ of an alpha carbon and the __________________ of a 3-oxocarboxylic acid.
alkylation, decarboxylation
Malonic Ester Mechanism
Acetoacetic Ester Synthesis
The product of the acetoacetic ester synthesis is a ______________ __________________.
methyl ketone
Mechanism for the intramolecular claisen (Dieckman)
Acyl chlorides can react with what to form what?
1) alcohols to form esters
2) water to form carboxylic acids
3) amines to form amides
2) water to form carboxylic acids
3) amines to form amides
Acyl chloride reaction with amines to form amides require ___________ equivalents of the _______________.
two, amine
The first to attack and the second to deprotonate the intermediate
Esters can react with what to form what?
1) water to form carboxylic acids
2) alcohol to form new ester
3) amine to form amide (1 equivalent)
2) alcohol to form new ester
3) amine to form amide (1 equivalent)
Reaction of an ester with an amine must be in what environment and why.
basic to avoid the protonation of the amine.
Ester hydrolysis is an _______________ catalyzed process which also has protonation of the leaving group.
acid
How does an acid catalyst increase the rate of ester hydrolysis?
Increases formation of intermediate by protonating the carbonyl oxygen and increases the leaving ability of the LG by protonating it.
In the reaction of an ester with an alcohol, excess ______________ is required.
alcohol
Carboxylic acids react with what to form what?
1) alcohols to form esters
Amides DO NOT react with…
halides, alcohols, or water
Amides will react with water and alcohol under ______________ conditions
acidic / heat
An amide will react with acid and heat will form a
carboxylic acid
An alkyl halide can react with _______________ to form a nitrile which is then converted to a ______________ ________________.
cyanide, carboxylic acid
An acid anhydride reacts with water to form two equivalents of a ____________________ __________________.
carboxylic acid
Esters and Acyl chlorides undergo _______________ successive reactions to form _________________ ________________.
two, tertiary alcohols
Acyl chlorides undergo __________________ successive reactions with hydrides to form a ___________________ alcohol.
two, primary
An ester can be reduced to an aldehyde only by using ___________________ at _________________ Celsius.
DIBALH, -78
A Michael reaction involves the attack of an ___________________ on a ________________ carbon of an a,b-unsaturated ketone.
enolate, beta
Michael reactions form ________________ diketones.
1,5
Enolates are ____________ bases and therefore add _________,_________.
weak, 1,4
The Robinson Annulation combines the _______________ addition and the _____________ reaction.
Aldol, Michael
The product of a Robinson Annulation is a _________,___________-_____________________ ketone.
a,b-unsaturated
Setting up for the Robinson annulation.
Retro synthesis of Robinson Annulation
Reaction of an aldehyde/ketone with a secondary amine forms a ________________.
enamine
Enamines resemble and react the same as _______________.
enolates
Aldehydes and ketones can be alkylated/acylated at the alpha carbon through an _______________ intermediate.
enamine
Using an enamine allows formation of a ___________________ alkylated product without using LDA.
monoalkylated
Enamine can also act as an enolate and attack the ________________ position of an a,b-unsaturated.
beta
The Diels-Alder reaction is a _________,__________ addition reaction.
1,4
A Diels-Alder reaction involves a conjugated _______________ and a ______________.
diene, dienophile
The reactivity of a dienophile is increased if an electron ___________________ group is attached to one of its sp2 carbons.
withdrawing
If the dienophile has two carbon carbon double bonds, _________________ successive reactions occur
two
What are the five common electrophilic aromatic substitution reactions
1) halogenations
2)nitration
3) sulfonation
4) Friedel-Crafts acylation
5) FC alkylation
2)nitration
3) sulfonation
4) Friedel-Crafts acylation
5) FC alkylation
The _____________ acidic the proton, the _____________ enolate is formed.
more, more
Acid catalyzed ester hydrolysis produces a
carboxylic acid
What is an enamine
tertiary a,b-unsaturated amine
What reagents are used to remove the enamine protecting group?
acid and water
In a Diels-Alder reaction, when the conjugated diene is in the locked s-cis cyclic position, the product is a _____________________ bicyclic compound.
bridged
Which is formed faster, the endo or exo product in a diels alder?
Endo is formed faster when the dienophile has a substituent with pi electrons.
What reagents are required to activate the electrophile for bromination
Br2 + FeBr3
What reagents are required to activate the electrophile in nitration
HNO3 + H2SO4
What is the electrophile in nitration reactions
NO2+ (nitronium ion)
What reagents are required to activate the electrophile for sulfonation
H2SO4+ and heat
What is the electrophile in sulfonation reations
SO3H+ (sulfonium ion)
FC acylation does what to a benzene ring
places an acyl group on it
What is the electrophile in a FC acylation
acylium ion (R-C+=O)
How is the electrophile for FC acylation activated?
an acyl chloride (Cl) attacks the Al of AlCl3 and the Cl is then eliminated.
What happens to primary carbocations?
they rearrange
How can a benzene substituted with a straight-chain alkyl group be formed?
Through acylation reduction
What are the three different sets of reagents used to reduce a carbonyl to a methylene group?
1) H2 / Pd C
2) Zn(Hg), HCl, heat – acidic
3) H2NNH2, OH-, heat – basic
2) Zn(Hg), HCl, heat – acidic
3) H2NNH2, OH-, heat – basic
Which reducing reagents can reduce all carbonyl compounds
Clemmensen and Wolff-Kishner
What are the reagents in the Clemmensen reduction
Zn(Hg), HCl, heat – acidic
What are the reagents in the Wolff-Kishner reduction?
H2NNH2, OH-, heat – basic
What is the stipulation to use H2 / Pd,C
Only a ketone carbonyl adjacent to a benzene ring can be reduced
What is the slow step of EAS?
addition of the electrophile to the nucleophilic aromatic ring
What will increase the rate of the slow step (addition of electrophile) of EAS?
A substituent that makes benzene a better nucleophile (electron donating)
The transition state of EAS resembles what?
the carbocation intermediate
What are moderately activating substituents?
Can donate electrons in two directions. To the ring and away.
What are moderately deactivating substituents?
Carbonyl group attached to ring.
What are strongly deactivating substituents?
positive charge attached to ring
What are strongly activating substituents?
Donate electrons to ring only – OR attached
What are halogen substituents?
weakly deactivating
All activating and weakly deactivating direct…
ortho and para
All substituents with a positive or partial positive attached to the ring direct _________________.
meta
The mirror image of a D-sugar is a ________ sugar
L
What is the Fisher projection of D-glucose
What are epimers?
Diastereomers that differ in configuration at only one asymmetric center
What is the Haworth Projection of D-glucose?
Groups on the Left in a Fisher are ____________ in a Haworth.
up
Groups that are Right on the Fisher are ___________ in a Haworth.
down
Two sugars that differ in configuration only at the carbon that was the carbonyl carbon in the open chain form are called ______________.
anomers
In the alpha anomer, the -OH group is ____________.
down (trans to the primary alcohol)
In the beta anomer, the -OH group is ____________.
up (cis to the primary alcohol)
In the Fisher projection, R equals ___________ and S equals __________.
D, L
To draw the Haworth, lay the Fisher down on its _________________ side.
right
The -OH on the number ____________ carbon attacks the carbonyl carbon.
five
What is the chair conformation of B-D-glucose.
The acetal of a sugar is called a ______________.
glycoside
The bond between the anomeric carbon and the alkoxy oxygen is a ________________ bond.
glycosidic
What is the mechanism for a glycoside formation?
Acetals are _____________________ sugars.
non reducing
What is an alpha-1,4-glycosidic linkage?
What is a beta-1,4-glycosidic linkage?
Acyl chlorides only react with alcohol and water
Grignards do not react with ______________ or _______________.
carboxylic acids, amides
When you see an alcohol with 2 identical groups, think __________________.
Grignard
What reagent converts an alcohol into a carboxylic acid?
What reagents synthesize an alcohol to an alkyl chloride?
Thionyl chloride.
What reagents synthesize an acid chloride from a carboxylic acid?
Thionyl chloride in pyridine.
How does LiAlH4 react with benzoyl chloride?
How does LiAlH4 react with acetic benzoic anhydride?
How does LiAlH4 react with benzoic acid?
How does LiAlH4 react with methyl benzoate?
How does LiAlH4 react with benzamide?
What product is formed when 2-bromohexane reacts with KCN, DMSO followed by H30+ and heat?
What is the product of hydrolysis of an acid chloride?
What is transesterification?
What is the product of an acid anhydride treated with an alcohol under acidic conditions?
What reagent(s) will reduce an ester to an aldehyde?
Di-Isobutyl Aluminum Hydride (DIBAH)
How does butyramide react with ethanol in acidic solution?
What reagents converts a ketone to an enolate? What is it used for?
With an enolate, an alkyl substituent group can be added. LDA will alkylate on the less-hindered side of C=O.
Show the synthesis of a carboxylic acid from a malonic ester.
What is decarboxylation?
Decarboxylation is the loss of CO2.
What is an enamine?
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine.
What is the “Michael Reaction” and draw the mechanism.
The “Michael Reaction” or “Michael addition,” is the nucleophilic addition of a carbanion or another nucleophile to an α,β unsaturated carbonyl compound. It belongs to the larger class of conjugate additions.
Draw a mechanism for a base-catalyzed aldol condensation.
Draw a mechanism for an acid-catalyzed aldol condensation.
Draw a mechanism for the base-catalyzed dehydration of an aldol.
What is an iminium salt intermediate and give a mechanism?
What is the product when ethenylbenzene is treated with KMnO4 and aq. NaOH?
What is the claisen condensation? Draw a mechanism.
A claisen condensation is a carbon-carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone.
*ALKENE REACTIONS*
*ALKENE REACTIONS*
Hydration: Reagants
Strong Acid, H20
Hydration: Products
Alcohol
(Regioselective: Markovnikof)
(Regioselective: Markovnikof)
Oxymercuration/Demercuration: Reagents
1. Hg(OAc)2, H2O 2. NaBh4, NaOH
Oxymercuration/Demercuration: Products
Alcohol
(Regioselective: Markovnikof)
(Regioselective: Markovnikof)
Addition of a Hydrogen Halide: Reagents
H-X
Addition of a Hydrogen Halide: Products
Alkyl Halide
(Regioselective: Markovnikof)
(Regioselective: Markovnikof)
Hydrogenation: Reagents
H2, Pt
Hydrogenation: Products
Alkane
(Stereospecific: Syn)
(Stereospecific: Syn)
Cyclopropanation: Reagents
Carbene
Cyclopropanation: Products
Cyclopropane
(Stereospecific: Syn)
(Stereospecific: Syn)
Epoxidation: Reagents
mCPBA
Epoxidation: Products
Epoxide
(Stereospecific: Syn)
(Stereospecific: Syn)
Acid-Catalzyed Epoxide Ring Opening: Reagents
H30
Acid-Catalzyed Epoxide Ring Opening: Products
Diol
(Stereospecific: Anti)
(A diol contains two hydroxyl groups)
(Stereospecific: Anti)
(A diol contains two hydroxyl groups)
Syn-Dihydroxylation: Reagents
OsO4, H2O2
Syn-Dihydroxylation: Products
Diol
(Stereospecific: syn)
(Stereospecific: syn)
Formation of a Halohydrin: Reagents
X2, H2O
Formation of a Halohydrin: Products
Halohydrin ( functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms)
(Stereospecific: Anti)
(Regioselective: Mark addition of -OH)
(Stereospecific: Anti)
(Regioselective: Mark addition of -OH)
Addition of X2: Reagents
X2
Addition of X2: Products
Vicinal Dihalde
(Stereospecific: Anti)
(Stereospecific: Anti)
Addition of HBr and Peroxides: Reagents
HBr, H2O2
Addition of HBr and Peroxides: Products
Alkyl Bromide
(Regioselective: Anti-Mark)
(Regioselective: Anti-Mark)
Hydroboration/Oxidation: Reagents
BH3,THF
Hydroboration/Oxidation: Products
Alcohol
Stereospecific: Syn)
(Regioselective: Anti-Mark)
Stereospecific: Syn)
(Regioselective: Anti-Mark)
Oxidative Cleavage: Reagents
KMnO4, Base
Oxidative Cleavage: Products
Ketones and Carboxylic Acids
Ozonolysis, Reductive: Reagents
O3, Me2S
Ozonolysis, Reductive: Products
Ketones and Aldehydes
Ozonolysis, Oxidative: Reagents
H2O2, AcOH
Ozonolysis, Oxidative: Products
Ketones and Carboxylic Acids
Grignard: Reagents
a. Mg, Ether b. Carbonyl c. strong acid
*OR*
a. LI Alkane, Ether b. Carbonyl c. strong acid
*OR*
a. LI Alkane, Ether b. Carbonyl c. strong acid
Grignard: Products
Alcohol
(Regioselective: Reagent adds to the Carbonyl)
(Regioselective: Reagent adds to the Carbonyl)
*ALKYNE REACTIONS*
*ALKYNE REACTIONS*
Synthesis of Dihalides: Reagents
NaOH, 200C *OR* NaNH3, H20
Synthesis of Dihalides: Products
Alkyne
Acetylide Anion: Reagents
Strong Nucleophile, H20
Acetylide Anion: Products
Alcohol
Oxidation of an Internal Alkyne: Reagents
KMnO4, H2O
Oxidation of an Internal Alkyne: Products
Dicarbonyl
Oxidation of an Terminal Alkyne: Reagents
KMnO4, H2O
Oxidation of an Terminal Alkyne: Products
Carboxylic Acid with adjacent Ketone
Hydrogenation (Alkyne): Reagents
H2, Pd
Hydrogenation (Alkyne): Products
Cis Alkene
(Stereospecific: Syn)
(Stereospecific: Syn)
Dissolving Metal Reduction: Reagents
Na(s), NH3, low temp
Dissolving Metal Reduction: Products
Trans Alkene
(Stereospecific: Anti)
(Stereospecific: Anti)
Ozonolysis: Reagents
O3, H2O
Ozonolysis: Products
Carboxylic Acids
Addition of HBr with Peroxides: Reagents
HBr, H2O2
Addition of HBr with Peroxides: Products
Vinyl Bromide
(Regioselective: Mark)
(Regioselective: Mark)
Addition of X2 (Alkyne): Reagents
X2, CH2Cl2
Addition of X2 (Alkyne): Products
Dohalide/Tetrahalide
(Stereospecific: Anti)
(Stereospecific: Anti)
Addition of HX: Reagents
HX, Ch2Cl2
Addition of HX: Products
Dihalide/Tetrahalide
(Regioselective: Mark)
(Regioselective: Mark)
Hydration (Alkyne): Reagents
HgSO4, H2SO4
Hydration (Alkyne): Products
Ketone
(Regioselective: Mark)
(Regioselective: Mark)
Hydroboration/Oxidaton: Reagents
SiaBH, H20, Strong Base
Hydroboration/Oxidaton: Products
Aldehyde
(Regioselective: Anti-Mark)
(Regioselective: Anti-Mark)