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WorksheetsOrganic Synthesis Quiz
Total questions: 24
Worksheet time: 13mins
What is the active oxidation state of the Pd catalyst in a Suzuki reaction?
-2
0
+2
+4
Compound A - pKa 2
Compound B - pKa 4
Compound A is...
2x more acidic than B
10x more acidic than B
100x more acidic than B
2x more basic than B
Which reagent would you use to reduce a carboxylic acid to an alcohol in presence of a ketone?
LiAlH4
BH3
NaBH4
Can't be done without protecting the ketone
Which is the first elementary step of a Suzuki reaction catalysed by Pd(PPh3)4?
Ligand exchange
Oxidative addition
Reductive elimination
Transmetallation
Which of these reactions contains a beta-hydride elimination step?
Heck
Sonogashira
Suzuki
All of the above
What is the oxidation state change for the iodine atom in a Dess-Martin oxidation?
I(V) to I(III)
I(III) to I(V)
I(III) to I(I)
I(I) to I(III)
Rank these N-heterocycles in order of basicity
A > D > C > B
A > B > C > D
A > C > D > B
A > C > B > D
Which of these reactions does not generate a C-C bond?
Stille
Buchwald-Hartwig
Sonogashira
Negishi
What is the name of this reaction?
Negishi
Stille
Kumada
Sonogashira
Which of these is not required in a Swern oxidation?
DMF
DMSO
Oxalyl chloride
Triethylamine
What is the name of this compound?
Cholecalciferol (Vitamin D)
Biotin (Vitamin B7)
Pantothenic acid (Vitamin B5)
Ascorbic acid (Vitamin C)
Which is the most acidic proton in this molecule?
A
B
C
D
Rank the following silyl protecting groups in order of stability in acid:
TIPS > TBDPS > TBS > TES
TBDPS > TBS > TIPS > TES
TIPS > TBS > TBDPS > TES
TBDPS > TIPS > TBS > TES
What's the name of this molecule?
1-Cl-6-Br-quinazoline
1-Cl-6-Br-phthalazine
4-Cl-7-Br-quinazoline
4-Cl-7-Br-phthalazine
Rank these heterocycles in order of SNAr reactivity
C > B > D > A
D > B > A > C
B > A > C > D
D > C > B > A
Which of the following heterocycles can you not synthesise from hydrazine?
Pyrazine
Pyrazole
Pyridazine
Phthalazine
Which of these is not a 1,3-dipole?
Carbonyl ylide
Sulfur ylide
Diazomethane
Ozone
What is the name of this reaction?
Fischer synthesis
Vilsmeier reaction
Hantzsch synthesis
Mannich reaction
What's the name of this molecule?
5-chloro-2-methylthiazole
5-chloro-2-methylisothiazole
4-chloro-2-methylisothiazole
4-chloro-2-methylthiazole
Which of these structures corresponds to the TosMIC reagent?
A
B
C
D
Which one of these alcohol protecting groups would be orthogonal to a N-Boc?
O-PMB
O-MOM
O-THP
O-TMS
Which of these peptide coupling reagents doesn't require an additional base?
HATU
DCC
CDI
T3P
Which pair of protecting groups will result in a shorter overall synthesis?
A = THP, R = Bn
A = Cbz, B = Me
A = Boc, B = tBu
A = Cbz, B = Bn
Which product would you expect from this three step sequence?
A
B
C
D
