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How can an aldehyde be protected? -CORRECT ANSWER Using a diol and H+
What does permanganate do? (KMnO4, NaOH) -CORRECT ANSWER Oxidizes
aldehydes and primary alcohols to carboxylic acids
How can an acetal (being used as a protecting group) be hydrolyzed back to its original
form? -CORRECT ANSWER H2O and H+ and heat
At what frequency is an OH or NH bond in IR spec? -CORRECT ANSWER 3400
At what frequency is a CH (sp3) bond in IR spec? -CORRECT ANSWER 3000-2850
At what frequency is a CH (sp2) bond in IR spec? -CORRECT ANSWER 3100-3000
At what frequency is a CH (sp) bond in IR spec? -CORRECT ANSWER 3300
At what frequency is a C-C triple bond or C-N triple bond in IR spec? -CORRECT
ANSWER 2100
At what frequency is C=O bond in IR spec? -CORRECT ANSWER 1700
At what frequency is a C=C bond or aromatic C-C bond in IR spec? -CORRECT
ANSWER 1600
At what frequency is an aromatic C-C bond in IR spec? -CORRECT ANSWER 1500
At what frequency is carboxylic acid in IR spec? -CORRECT ANSWER 1720 + a strong
and broad band at 2500-3300
At what frequency is an amide bond in IR spec? -CORRECT ANSWER two medium
strength bands around 3400 + the carbonyl band below 1700
At what frequency is a sp3 C atom in a proton NMR spec? -CORRECT ANSWER 1
At what frequency is a C atom attached to a pi system in a proton NMR? -CORRECT
ANSWER 2
, At what frequency is a C atom attached to an O atom in a proton NMR? -CORRECT
ANSWER 3-4
At what frequency is a sp2 C atom in a proton NMR? -CORRECT ANSWER 5-6
At what frequency is an aromatic C atom in a proton NMR? -CORRECT ANSWER 7-8
At what frequency is an aldehyde C atom in a proton NMR? -CORRECT ANSWER 10
At what frequency is a carboxylic O atom in a proton NMR? -CORRECT ANSWER 11-
12
At what ppm is a sp3 alkyl C atom in carbon NMR? -CORRECT ANSWER 10-30
At what ppm is a sp3 C atom attached to O, N, or X in carbon NMR? -CORRECT
ANSWER 50-70
At what ppm is an sp C atom in carbon NMR? -CORRECT ANSWER 75-90
At what ppm is a sp2 C atom in carbon NMR? -CORRECT ANSWER 100-150
At what ppm is an ester, amide, or carboxyl C=O in a carbon NMR? -CORRECT
ANSWER 160-180
AT what ppm is an aldehyde or ketone C=O in a carbon NMR? -CORRECT ANSWER
190-200
What are examples of oxidizing agents? -CORRECT ANSWER Chromium (VI) reagents
like CrO3, K2Cr2O7, K2CrO4; and a manganese (VII) reagent (KMnO4).
Chromium reagents = acidic conditions
Manganese reagent = basic conditions
Which anhydrous chromium (VI) reagents can stop oxidation of primary alcohols at the
aldehyde stage? -CORRECT ANSWER CrO3--2 pyridine (chromium trioxide-pyridine
complex), PCC (pyridinium chlorochromate) and PDC (pyridinium dichromate)
In oxidative cleavage reactions, what reagents will cleave vicinal diols, alkenes, and
methyl ketones? -CORRECT ANSWER Vicinal diols = HIO4 (periodic acid)
Alkenes = ozone
Methyl ketones = alkaline solutions of the halogens (haloform reaction)
In oxidative addition products of alkenes and alkynes, which reagents can be used? -
CORRECT ANSWER Cold, alkaline permanganate, osmium tetroxide and proxy acids.