OCHEM 316 - Organic Chemistry II » Summer 2022 » Exam 1 Module 1-6

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Question #1
Butane, C4H10, would have which of the following fragments in its mass spectrum? m/z I 15 II 29 III 57
A.   I
B.   II
C.   III
D.   I and II
Question #2
Pentane, C5H12, would have which of the following fragments in its mass spectrum? m/z I 29 II 43 III 57
A.   I
B.   All of the choices are correct
C.   II
D.   III
Question #3
Which of the following statements about the base peak of a mass spectrum is always true?
A.   The base peak corresponds to the most abundant ion
B.   The base peak corresponds to the lowest m/z
C.   None of these
D.   The base peak corresponds to the molecular ion
Question #4
You observe a compound that exhibits a mass spectrum with peak at 160 and a peak at 162, both of equal intensity. This compound contains
A.   two bromine atoms
B.   one bromine atom
C.   one iodine atom
D.   two chlorine atoms
Question #5
What would be the molecular formula of rose oxide which contains C, H, and O and has two degrees of unsaturation and a molecular ion in its mass spectrum at m/z =154?
A.   C9H14O2
B.   C8H10O3
C.   C10H18O
D.   C10H2O2
Question #6
Why does an alkyne carbon–carbon triple bond vibrate at a higher wavenumber than an alkene carbon–carbon double bond?
A.   It has fewer hydrogens
B.   It is stronger
C.   It is weaker
D.   It makes a less stable cation
Question #7
Which of the following information is primarily obtained from an IR spectrum?
A.   Conjugated  p system present in a compound
B.   Molecular weight of a compound
C.   The carbon and hydrogen framework of a compound
D.   Functional groups present in a compound
Question #8
What is the purpose of a silyl ether?
A.   To protect esters from organometallic reagents and other reagents
B.   To prevent the formation of carboxylic acids
C.   To protect ketones from organometallic reagents and other reagents
D.   To protect alcohols from organometallic reagents and other reagents
Question #9
Which reagent can be used to reduce an acid chloride to an aldehyde?
A.   NaBH4
B.   LiAlH4
C.   LiAlH(OtBu)3
D.   FeCl3
Question #10
Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde?
A.   A ketone has no C-H stretches
B.   An aldehyde has two C-H stretches between 2700-2850 cm−1
C.   A ketone has no carbonyl stretch at 1720 cm−1
D.   An aldehyde has a carbonyl stretch at 1820 cm−1
Question #11
What is the overall charge of the amino acid, alanine, at pH = 10?
A.   no overall charge
B.   -2
C.   1
D.   -1
Question #12
What two groups make up the carboxylic acid group (RCOOH)?
A.   Carbonyl oxide and hydrogen
B.   Carbon dioxide and hydrogen
C.   Carbon monoxide and hydroxyl
D.   Carbonyl and hydroxyl
Question #13
Which of the following is the most polar organic compound?
A.   CH3COOH
B.   CH3CH2CH2CH3
C.   CH3CH2CH2OH
D.   CH3CH2CHO
Question #14
Which of the following statements about amides is true?
A.   Amides do not react under any conditions. They are inert compounds
B.   Amides react with methyl alcohol in the presence of an acid catalyst to form an ester
C.   Amides react with thionyl chloride to form the acid chloride
D.   Amides are hydrolyzed in acid or base to form carboxylic acids or carboxylate anions
Question #15
All of the following contain sp2 hybridized atoms in their functional group except
A.   an anhydride
B.   an aldehyde
C.   a carboxylic acid
D.   a nitrile
Question #16
From the list below, pick the compound that does not react with acetyl chloride.
A.   Ammonia
B.   Benzoic acid
C.   Isopropyl alcohol
D.   Triethyl amine
Question #17
Why is pyridine included in the reaction of an acid chloride and an amine or alcohol?
A.   Pyridine will deprotonate the amine or alcohol, making it a better nucleophile
B.   Pyridine will neutralize the acid by-product of the reaction
C.   Pyridine will absorb the heat of the reaction
D.   Pyridine will protonate the carbonyl of the acid chloride, making it more reactive

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