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19 Cards in this Set

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  • Back
What is PCl5 used for?
To create acid chlorides from carboxylic acids.
1) What happens when adding SOCl2 (thionyl chloride) to a carboxylic acid?

2) What else can SOCl2 be used for?
1) It creates an acid chloride.

2) To cause substitution. It turns an alcohol into a chloride. This is good to use when converting a primary alcohol to a primary alkyl halide or if another part of your molecule is sensitive to HCl. (verify this from Ochem 1)
What is P2O5 used for?
To convert carboxylic acids into anhydrides.
How do you convert carboxylic acids into anhydrides?
Using P2O5.
1) What is P2O5?

2) What does it do?
1) A desiccant.

2) It is used for dehydration, it converts carboxylic acids into anhydrides.
Describe an aldol condensation reaction:
1) Starting conditions
2) What type of reaction it is
3) Describe the product
1) Aldol condensation requires heat and an aldehyde plus a ketone (or another aldehyde)

2) Since it is a condensation reaction, it loses water. The aldehyde is lost as water and the ketone remains intact.

3) The product is an alpha-beta-unsaturated ketone.
How do you turn a primary alcohol into a primary alkyl bromide?

What about a primary alkyl chloride?
You can use PBr3 to convert to a primary alkyl bromide. This is better than just using HBr in some cases because it mostly avoids rearrangement and it won't affect other functional groups that are sensitive to acids.

Use SOCl2 to convert to a primary alkyl chloride.
What is the best way to convert an allylic alcohol into an aldehyde?
Use MnO2. The pathway has some free radical steps.
How do you convert a carboxylic acid into an aldehyde?
First convert it to an acid chloride with PCl5

Then reduce the acid chloride with H2, Pd/C and a poisoned catalyst (quinoline; Lindlar's).
Describe the Haloform reaction and what it is used for.
The haloform reaction breaks a carbon-carbon bond on a carbonyl compound.

It is done by adding NaOH and Br2 to a carbonyl which causes Bromine addition to the beta position.
What is required for side-chain oxidation of alkylbenzenes?

What is the purpose?
It requires that the alkyl substituent has at least one benzylic hydrogen. You can use either Jones reagent under harsh conditions or KMnO4 (potassium permanganate).

It turns the chain, regardless of size, into a carboxylic acid.
How do you convert a nitrile into a carboxylic acid?

What is the other product?
With water, hydroxide and heat.


With acid, 2 equivalents of water and heat.

The other product is ammonium ion.
What are the conditions for the Haloform reaction?

What is it used for?
It requires an aldehyde or a ketone (with alpha hydrogens), 3 equivalents of diatomic bromine (Br2) and a base. This must be followed by an acidic workup.

It is used to cleave a carbon-carbon bond.
What is the purpose of reductive amination?

What are the reaction conditions?

Why is it preferred over direct alkylation of amines?
It is used to alkylate amines.

It requires a WEAK acid (such as acetic acid), NaBH3CN (sodium cyanoborohydride) and a carbonyl containing the alkyl chain that you wish to add, such as an aldehyde (the carbonyl oxygen is lost as water).

It is preferred because it adds one alkyl group at a time. Direct amination goes kind of crazy, creating a plethora of mixed products.
What is the difference between an Aldol Condensation and a Claisen Condensation?
Claisen creates an anhydride while Aldol creates an alpha-beta-unsaturated ketone.
What is NBS and what is it used for?

What are the required conditions?
N-Bromosuccinimide. It's used to make a free-radical beta-addition of bromine to an allylic compound. (The bromine adds beta to the double-bond).

The required conditions are heat or light, NBS and peroxides (a free radical initiator).
What is the purpose of DMAP?
It converts anhydrides to esters.
What are the conditions required for Fischer Esterification?
Carboxylic acid
The alcohol containing the R group you'd like to add (this must be present in excess).
What is the use of DMAP?

What else is needed in the reaction?

What is the purpose of each item?
DMAP converts anhydrides to esters and carboxylic acids.

It requires DMAP, an anhydride, an alcohol containing the R group you'd like to add and Et3N.

The purpose of the Et3N is to deprotonate the carboxylic acid at the end. This is important because the carboxylic acid would otherwise protonate the other product and reverse the reaction.