Reactions of Organic Chemistry II

H₃O+ (hydronium ion) and a nucleophile like CN or OH

What are some typical reagents for acid catalyzed hydration

H₂O, an electrophile like CN

What are some reagents for base catalyzed hydration

LiAlH₄, NaBH₄, Ni, Pd/C & H₂

What are some reduction reagents for ketones/aldenhydes?

These are the reactants of the addition of HCN, what is the product?

These are the reactants of the addition of H₂O, what is the product?

Aldenhydes

What do primary alcohols oxidize to?

Ketones

What do secondary alcohols oxidize to?

Cr₂O₇, CrO₃, PCC/CH₂Cl₂, MnO₂

What are some reagents for oxidation overall?

What is the product for a secondary alcohol with these reagents?

What is the product for a secondary alcohol with these reagents?

What is the product for a secondary alcohol with these reagents?

AlCl₃,H₂O

What are the reagents for Friedel-Crafts Acylation?

Hg²⁺, H₂SO₄

What are the reagents for the hydration of alkynes?

What is the product for this Friedel’s Craft Acylation

What is the product for the Hydration of Alkynes?

THF, H₂O₂/OH

What are the reagents for the hydroboration-oxidation of alkynes

What is the product for the Hydroboration-oxidation of Alkynes?

LiAlH₄, NaBH₄

What are some reduction reagents that should be known in aldehydes and ketones?

What is the product for this reduction reaction (ketone)

What is the product for this reduction reaction (ketone)

What is the product for this catalytic Hydrogenation

What is the product for this catalytic Hydrogenation

Pd/C, Ni Catalyst

What are some reagents for catalytic hydrogenation?

HBr or Ph₃PBr₂ along with Mg/ether

What reagents can help a Grignard reagent form?

It will turn it into an alcohol

How will an MgBr react with a ketone?

They also form alcohols

How do orgolithium reagents react with ketones?

How do acetylide reagents react with ketones?

With the reaction of an aldenhyde or a ketone & an alcohol with a prescence of a strong acid

How are acetals formed?

What does this acetal formation reaction form?

They are strong protecting groups

Why are acetals good in synthesis?

AcO, heat

What are the reagents for imine and enamines formation

What is the reaction product for this imine formation

What is the reaction product for this enamine formation

Acid

What are the reagents for enamine formation?

Wolff-Kischner Reaction/Clemmensen Reaction

These reactions can be used to reduce aldenhydes and ketones to a methylene

What is the reaction product for this wolff-kischner reaction?

H₂N-NH₂, KOH, and heat

What are the reagents for Wolff-Kischner Reaction?

Zn/Hg, HCl

What are the reagents for Clemmensen Reaction?

What is the reaction product for this clemmensen reaction?

Wittig Alkene Synthesis

This is a good reaction to prepare alkenes from aldenhydes and ketones

Ph₃PCH₃

Reagents for Wittig Alkene Synthesis?

Reaction product for Wittig Alkene Synthesis?

KMnO₄/NaOH, H₂Cr₂O₇, and Ag₂O

What are some good reagents for the oxidation of aldehydes?

Yes espeically if ortho para groups are added

Are allylic and benzylic radicals are good at reacting?

NBS Reactions

This is a reaction where there is a slower release of bromination as Br₂ concentration remains low

What are the products for this NBS reaction

H₂CrO₄,H₂O or AgO and KMnO₄

What are the reagents for the oxidation of alcohols and aldenhydes?

What is the reaction product for this oxidation of primary alcohol and aldenhyde?

CH₃OH or CH₂N₂ & H₂SO₄

What are the reagents for an acid/fischer esterfication

What is the product of this Fischer Reaction?

SOCl₂ & PCl₅

What are the reagents for Acid Chloride formation?

What is the reaction product of the synthesis of acid chlorides?

Through the treatment of sodium salts with PCl₅

How are sulfonyl chlorides prepared?

LiAlH₄

How can carboxylic acids be reduced to a primary alcohol?

CO₂

What does the carboxylic acid lose during decarboxylation?

SN₁ or SN₂

What are the reactions that vinylic or phenols can’t really react to?

They would have to rehybridize and also steric hinderance being an issue with the bond angle changing from 120 to 90

Why can’t vinyls or phenols really react in SN reactions?

L type ligands

These are the type of ligands that can be removed with its bonding electron pair and obtain a neutral molecule

X type ligands

Those that we can remove with its bonding pair having formal charge

X type ligand

This ligand can be removed with its bonding pair that has a molecule with formal charge

Pd(OAc)₂

Reagents for the Heck reaction

Reaction product for heck reaction

Pd(OAc)₂, PPh₃, Na₂CO₃

What are the reagents for suzuki coupling

What is the product for this suzuki coupling?

Adding an ortho para directing group to the phenol

What makes phenol extremely reactive?

Acid chlorides and anhydrides

These will react rapidly with water even in the absence of bases

Reaction product for hydrolysis of acid chloride and anhydrides

Hydrolysis of esters/saponofication

This reaction is irreversible unlike the acid version of this reaction.

Through an acid catalyst and when the OHs meet up

How can lactones be formed?

Through strong acids and heat

How can nitriles and amides be hydrolyzed to carboxylic acids?