CHM 234 Exam 3

Which of the following reactants will NOT undergo benzylic oxidation when treated with KMnO4?
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Which compounds are classified correctly?
Alcohol, ether, ketone
Alcohol, carboxylic acid, aldehyde
Amide, aldehyde
Which of the following is the correct IUPAC name for the following structure?
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Lithium 3-methylbutanoate
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Lithium hexanoate
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Potassium Pentanoate
Select the correct synthetic sequence to accomplish the following transformation.
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2.Br2, hv 3.(CH3)3COK 4.1.BH3, THF 2.H2O2/NaOH/H2O 5.PCC
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2. Br2, FeBr3 3.Zn-Hg, HCl 4.Br2,hv
Predict the major product for the following reaction
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Cl2/FeCl3
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HNO3/H2SO4
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Br2/FeBr3
Rank the following in order of increasing acidity (least acidic to most acidic)
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What would be the expected outcome if one equivalent of NaBH4 were reacted with the molecule shown below?
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Greater distribution of addition at X
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Greater distribution of addition at Y
Which of the following is the final major product of the following synthetic sequence
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Which of the following is the final major product of the following synthetic sequence
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Benzyl alcohol
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Benzoic acid
What is the major product formed in the following reaction?
(CH3)2CHCH2CH2Br = 4-methylpentanoic acid
(CH3)3CCH2CH2Br = 4,4-dimethylpentanoic acid
At which site on the following substrate will electrophilic substitution be most likely to occur, in the formation of a mono-substitutued product?
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Select the product of the following reaction
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Which of the following compounds will undergo nucleophilic acyl substitution reaction
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Which of the following compounds will undergo nucleophilic addition reaction
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Predict the product for the following reaction sequence.
2,5-octanediol
What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2 is treated with aqueous NaOH solution?
The salt of benzoic acid would dissolve ....
What is the driving force for losing a proton as the last step in electrophilic aromatic substitution?
To restore the aromatic system
How could you separate the following compounds?
Dissolve them in an organic solvent, then extract with a basic ....
Why are ketones less reactive than aldehydes?
Carbonyl carbon of ketones is less electron deficient due to electron
Ketones are more sterically hindered
Both
Which reagent can be used to reduce both double bonds in cyclopentenone
H2. Pd-C
What reagents would be used to selectively reduce the alkene in cyclopentenone
1 eq of H2, Pd-C
What reagents would be used to selectively reduce the C=O in cyclohexenone
LiAlH4
NaBH4
Both
Which hydrogen is the most acidic in the molecule shown below?
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