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36 Cards in this Set

  • Front
  • Back
What is the pKa of the following hydrogens?

Alkane (sp3)
Alkene (sp2)
Alkyne (sp)
Alkane ~55 (usually greater than)
Alkene 42
Alkyne ~25
What is this and what is its pKa?
Ammonia, pKa 35
What is this and what is its pKa?
Alcohol, pKa 15-19 depending on the structure of R
What is this and what is its pKa?
Thiol, pKa 10-12, depending on the structure of R.
What is this and what is its pKa?
Ammonium ion, pKa 9.25
What is this and what is its pKa?
Hydrocyanic acid, pKa 9.40
What is this and what is its pKa?
Carboxylic acid, pKa 1-5, depending on structure of R. Trifluoroacetic acid (HOOCCF3) has a pKa of less than 1 (about 0.5)
What is this and what is its pKa?
Trifluoroacetic acid, pKa ~0.50
What is this and what is its pKa?
Hydronium ion, pKa, -1.7
What is this and what is its pKa?
Sulfuric acid, pKa -3
What is this and what is its pKa?
Hydrochloric acid, pKa -6 to -7
What is this and what is its pKa?
Hydrobromic acid, pKa -8 to -9.5
What is this and what is its pKa?
Hydroiodic acid, pKa -9.5 to -10
What is this and what is its pKa?
Perchloric acid, pKa -10 (actual not known)
What is this and what is its pKa?
Ketone, pKa ~20
What is this and what is its pKa?
Allyl, pKa ~43
What is this? If R was a hydrogen, what is its pKa value?
A benzyl group, pKa 41
Name the functional group.
Ether
What is this and what is its pKa?
Aldehyde, pKa ~17
What is this and what is its pKa value?
Ketone, pKa ~20
Name the functional group
Allyl group
Name the compound
Enamine, this is the Nitrogen analog of an enol.
What is this and what is its pKa value?
Ester, pKa ~25
Name the compound.
Semicarbazide.
Name the functional group.
Acetal
Name the functional group.
Ketal
What is this and what is its pKa?
TsOH (p-toluenesulfonic acid), pKa ~ -1
What are the 4 categories of Carboxylic Acid reactions?
1) Reactions at the carbonyl group

2) Reactions at the carboxylate group

3) Loss of the carboxy group as CO2 (decarboxylation)

4) Reactions involving the α-carbon
Name the functional group.
Acyl chloride (acid chloride).
What is a lactone?
A cyclic ester.
What's the difference between an amine and an amide?
An amide has a carbonyl group, an amine does not.
What is the pKa of a protonated amine?
~10.6
What is this and what is its pKa value?
Amide
pKa ~15
What is this compound? How is it made?
Imine. It is made by reacting a primary amine with an aldehyde or ketone.
What is this compound? How is it made?
It is an enamine. "En-" for "alkene" (the nitrogen is attached to a carbon that is part of a double bond) and "amine" for the amine group. It is made by reacting a secondary amine with an aldehyde or a ketone.
What is this and what is it used for?
mCPBA (meta-chloroperbenzoic acid)

It is used to convert alkenes to epoxides.