Chemistry 222 - Test 2 Review Sheet
Naming Ethers, Thiols, Aldehydes, Ketones, Carboxylic Acids, Acyl Chlorides, Acid Anhydrides, Carboxylate
Salts, Esters, Amides
Recognizing ethers, epoxides, crown ethers, thiols, sulfides, disulfides, sulfoxides, sulfones, sulfonic acids,
aldehydes, hemiacetals, acetals, lactams, amines, imines, enamines, carboxylic acids, esters, thioesters,
amides, lactones, lactams, anhydrides, acyl chlorides, imides
Structures of pyridine, furan, tetrahydrofuran, dioxane
Relative acidities of carboxylic acids. Relative acidities of alpha hydrogens in carbonyl compounds.
Relative reactivities of acyl compounds in nucleophilic acyl substitution.
Which of these reagents (1-7) would react with each of these molecules (a-e):
1) H2O ; 2) CrO3, H2SO4 ; 3) EtMgBr ; 4) LiAlH4 ; 5) Dess-Martin ; 6) Ph3P=CH2 ; 7) SOCl2
a) Alcohol; b) Ether; c) Aldehyde; d) Ketone; e) Carboxylic Acid; f) Ester
Give the full name represented by these acronyms: DMSO; THF; MCPBA; DIBAH; NBS; TMS
Using the Grignard Reaction and protecting groups make each of the substances on the right from the two
substances on the left. (More than 1 step is required.)
OH OH
OH
Br
OH
O
O
OH
O
How would you make each of the two starting materials above from an alcohol.
(More than 1 step is required for halohydrin.)
Write the mechanism for the reaction shown below:
O
O
-
Cl
O
O
Fill in the missing starting materials, reagents, and products.
1) NaBH4
2) H 3O+
1) DIBAH
2) H 3O+
TosCl
OTos NaNH
2
pyridine
Br
1)
2) H2O
M gBr
O
1) H2 N
S
NH2
2) H2O,NaOH