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78 Cards in this Set
- Front
- Back
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If an alkyne is treated with H2/Pt the resulting product would be termed a _______
A. alcohol B. alkene C. alkyl halide D. alkane E. ether |
D. Alkane
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The intermediate formed in the addition reaction of HBr to an alkene has a carbon with a positive charge. This is called a carbocation. Carbocations function as _____ in polar organic reactions
A. bases B. anions C. nucleophiles D. electrophiles E. don't react |
D. electrophiles
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Which of the following molecules does exist as a cis/trans isomer pair?
A. 2-butene B. 1-butene C. 2-methyl-2-butene D. 2,3-dimethyl-2-butene E. all have cis/trans forms |
B. 1-butene
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Which of the following statements is true?
A. the cis form of an alkene is lower in energy than the trans form B. the trans form of an alkene is lower in energy than the cis form C. the cis form of an alkene is more stable than the trans form D. the trans form of an alkene is more stable than the cis form E. both b and d |
E. both b and d
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Bromine atoms add to opposite faces of the cyclohexene double bond, therefore we say that the reaction occurs with:
A. anti addition B. syn addition C. cis stereochemistry D. retention of addition |
A. anti addition
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What type of reactive intermediate is formed in the reaction of an alkene with Br2?
A. radical B. cyclic bromonium ion C. carbanion D. carbocation E. osmonium ion |
B. cyclic bromonium ion
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Which of the following alkenes is the most stable?
A. 1 B. 2 C. 3 D. 4 |
B. 2
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What type of reactive intermediate is formed in the reaction of an alkene with OsO4?
A. radical B. cyclic bromonium ion C. carbanion D. carbocation E. cyclic osmate |
E. cyclic osmate
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What is the correct order of decreasing oxidation level of the following compounds (higher oxidation level > lower oxidation level: Hint: Think of the "organic" definition of oxidation)?
A. 1>3>4>2 B. 1>2>3>4 C. 3>1>4>2 D. 3>1>2>4 E. equal in oxidation level |
D. 3>1>2>4
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If a reaction produces a product via an addition reaction, the reverse reaction to re-form the starting material can be considered a ______ reaction.
A. radical B. elimination C. addition D. rearrangement |
B. elimination
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A terminal alkyne can be treated with a _____ to produce an acetylide anion.
A. strong acid B. weak acid C. Mg D. strong base E. weak base |
D. strong base
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Acetylide anions will function as _____ in organic reactions.
A. nucleophiles B. electrophiles C. acids D. carbocations E. Grignard reagents |
A. nucleophiles
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When treated with acid and HgSO4 a terminal alkyne will formed a _____.
A. alcohol B. alkane C. alkene D. ketone E. aldehyde |
D. ketone
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When treated with BH3 followed by H2O2 a terminal alkyne will form a _____
A. alcohol B. alkane C. alkene D. ketone E. aldehyde |
E. aldehyde
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Regiochemical term describing the orientation of OH and H on the product resulting for the treatment of an alkene with BH3 followed by H2O2/-OH
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Non-markovnikov orientation
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Stereochemical term describing the orientation of OH atoms on the product resulting from an alkene with mCPBA following by H+
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anti-addition
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Stereochemical term describing the orientation of hydroxyl groups on the product resulting from treatment of an alkene with osmium tetraoxide and aqeuous NaHSO3.
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syn-addition
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Regiochemical term describing the orientation of OH and H on the product resulting for the treatment of an alkene with acid and water
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Markovnikov orientation
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Stereochemical term describing the orientation of H atoms on the product resulting from the treatment of an alkyne with Li/NH3
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anti-addition
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Stereochemical term describing the orientation of H atoms on the product resulting from the treatment of an alkyne with H2/ Lindlar catalyst
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syn-addition
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When CHCI3 is treated with KOH a ______ is formed
A. carbocation B. dichlorocarbene C. CH3OH D. cyclopropane E. no reaction occurs |
B. dichlorocarbene
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In the presence of an acid, an epoxide will form a
A. alcohol B. Ketone C. syn 1,2-diol D. anti 1,2-diol E. no reaction occurs |
D. anti-1,2,-diol
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Which of the following conditions would cleave the C=C of an alkene?
A. ozone/Zn B. KMnO4/base C. HIO4/H2O D. CH2I2/Zn E. mCPBA |
A. ozone/Zn
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Which of the following is not true regarding the conformation of substituted cyclohexanes?
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B. substituted cyclohexanes are stabilized by 1,3-diaxial interactions.
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Which of the following statements is true for (S)-(-)-Serine
A. is racemic B. rotates plane-polarized light in a counterclockwise direction C. rotates plane-polarized light in a clockwise direction D. is dextrorotatary |
B. rotates plane-polarized light in a counterclockwise direction
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A species that lies at an energy minimum between steps on a reaction
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reaction intermediate
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A reaction where delta G is negative
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exergonic reaction
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The energy needed by reactants to reach the transition state
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activation energy
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A molecule with 4 chirality centers will have how many possible isomeric forms?
A. 4 B. 8 C. 10 D. 14 E. 16 |
E. 16
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Describes organic molecules which rotate plane-polarized light
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optically active
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_____ is the property of "handedness"; the property of an object that causes it to be nonsuperimposable on its mirror image
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chirality
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_____ are stereoisomers that are not mirror images
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diastereomers
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_____ is the carbon atom in a molecule that is bonded to four different atoms or groups of atoms
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chirality center
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Molecules which contain chirality centers and are superimosable on their mirror image
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meso compounds
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Which of the following statements is true for the enantiomer of (s)-(-)-Serine
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It would be denoted (R)-(+)-Serine
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Which of the following statements is true?
A. All compounds and their mirror images are enantiomers B. superimposable structures are enantiomers C. all molecules that have chiral carbons are chiral D. Stereoisomers that are not superimposable on their mirror images are enantiomers E. a and c are true |
D
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Which of the following is the definition of a meso compound?
A. a chiral compound with more than one chirality center B. a molecule with chirality centers which is not superimposable on its mirror image C. a diastereomer with no chirality centers D. a molecule with chirality centers which is superimposable on its mirror image |
D. a molecule with chirality centers which is superimposable on its mirror image
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Which of the following words defines a species that forms a bond by donating an electron pair
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Lewis base
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In a neutral organic molecule, how many bonds will a carbon atom have?
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four
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In a neutral organic molecule, how many bonds will a nitrogen atom have?
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three
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In a neutral organic molecule, how many bonds will an oxygen atom have?
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two
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In a neutral organic molecule, how many bonds will a hydrogen atom have?
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one
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A double bond between a carbon atom and a nitrogen atom is comprised of how many sigma and pi bonds?
A. 1,0 B. 1,1 C. 1,2 D. 2,0 E. 2,1 |
B. 1,1
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A triple bond between two carbons is comprised of how many sigma and pi bonds?
A. 1,0 B. 1,1 C. 1,2 D. 2,0 E. 2,1 |
C. 1,2
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A single bond between a carbon atom and a hydrogen atom is comprised of how many sigma and pi bonds?
A. 1,0 B. 1,1 C. 1,2 D. 2,0 E. 2,1 |
A. 1,0
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Which of the following concepts would account for the greater acidity of acetic acid as compared to ethanol?
A. acetic acid has more carbons B. acetic acid has a hydrogen atom bonded to an oxygen atom C. there are more resonance structures that can be drawn for the acetate anion formed when acetic acid loses a proton D. any molecule with a carbonyl group must be more acidic than an alcohol E. the question is invalid as acetic acid is less acidic than ethanol |
C
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Which of the following molecules is the strongest acid?
A. 4-methylphenol (pKa = 10.17) B. n-butyl alcohol (pKa = 18) C. 4-chlorophenol (pKa = 9.2) D. water (pKa = 15.7) E. ethyl alcohol (pKa = 15.9) |
C. 4-chlorophenol (pKa = 9.2)
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When two electrons in orbitals that are parallel to one another combine to form a covalent bond this is termed a ____ bond
A. single B. double C. triple D. sigma E. pi |
E. pi
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Which of the following is not true about resonance structures?
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resonance forms result from the movement of sigma or non bonding electrons
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In which series are the elements listed in order of increasing electronegativity?
A. N<P<Br B. Cl<S<P C. As<S<F D. C<Si<Ge E. all atoms have the same electronegativity |
C. As<S<F
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Which of the following functional groups contains a carbonyl group?
A. ketone B. amide C. carboxylic acid D. ester E. All of the above |
E. All of the above
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Alkanes can be describes as
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Saturated hydrocarbons
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If an acid/base reaction occurs in the forward direction the product conjugate acid in the reaction must
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Be weaker than the starting acid
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The hybridization of oxygen in the water molecule is
A. sp B. sp2 C. sp3 D. hybridized E. sp4 |
C. sp3
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Concentration of the leaving group molecule effects rate.
A. Sn1 B. Sn2 C. both D. neither |
c. both
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Concentration of the nucleophile effects rate
A. Sn1 B. Sn2 C. both D. neither |
B. Sn2
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Is a 1 step mechanism.
A. Sn1 B. Sn2 C. both D. neither |
B. Sn2
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Is a 3 step mechanism
A. Sn1 B. Sn2 C. both D. neither |
D. neither
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The second step is rate determining.
A. Sn1 B. Sn2 C. both D. neither |
D. neither
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The rate is enhanced by polar protic solvents.
A. Sn1 B. Sn2 C. both D. neither |
A. Sn1
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Can lead to a racemic mixture of products.
A. Sn1 B. Sn2 C. both D. neither |
A. Sn1
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Retains initial stereochemistry in products.
A. Sn1 B. Sn2 C. both D. neither |
D. neither
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Rate is enhanced by better nucleophile
A. Sn1 B. Sn2 C. both D. neither |
B. Sn2
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Final product can arise from carbocation rearrangements.
A. Sn1 B. Sn2 C. both D. neither |
A. Sn1
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Which of the following would be the best solvent for an Sn2 reaction?
A. ethanol B. water C. methanol D. DMF E. acetic acid |
D. DMF
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The kinetics of a Sn2 reaction are considered?
a. not measurable b. zero order c. first order in [alkyl halide] d. first order in [nucleophile] E. both c and d |
E. both c and d
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Which of the following alkyl halides undergoes the fastest Sn2 reaction with NaOCH3?
a. 1-fluorobutane b. 1-chlorobutane c. 1-iodobutane d. 1-bromobutane |
C. 1-iodobutane
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A Sn1 reaction is performed twice. In the second experiment the concentration of the nucleophile is
doubled (compared to the first experiment). What effect would this have on the overall rate of the reaction? a. second reaction occurs twice as fast as the first experiment b. second reaction occurs 3/2 as fast as the first experiment c. second reaction occurs 1/2 as fast as the first experiment d. second reaction occurs 2/3 as fast as the first experiment e. both reactions occur at the same rate |
E. both reaction occur at the same rate
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Assuming the molecule undergoes a nucleophilic substitution reaction with H20, the final product is
classified as a(n) _________ _ a. aldehyde b. ketone c. carboxylic acid D. alcohol e.amine |
D. alcohol
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Assuming the molecule undergoes a nucleophilic substitution reaction in a polar, aprotic solvent such as
DMF with -oH, the stereochemistry of the final product will be? a. 3S, 4R b. 3R, 4R c. 3S, 4S d. 3R, 4S e. both a and b |
D. 3R, 4S
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Assuming the molecule undergoes a nucleophilic substitution reaction in a polar, protic solvent such as
methanol with -oH, the stereochemistry of the final product will be? a. 3S, 4R b. 3R, 4R c. 3S, 4S d. 3R, 4S e. both a and b |
E. both a and b
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Comparing the molecule as shown (no reaction) to its mirror image (not shown) the relationship would be
termed a. diastereomers b. enantiomers c. meso d. constitutional isomers |
B. enantiomers
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For a diene to undergo a Diels-Alder reaction it must:
a. be substituted with electron-withdrawing groups b. be able to adopt an s-trans conformation c. be substituted with electron-donating groups d. be able to adopt an s-cis conformation e. have more than 6 carbons |
D. be able to adopt an s-cis conformation
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Electrophilic addition reaction of conjugated dienes that occur at low temperature and/or short reaction
times (irreversible conditions) are said to be under: a.1 ,2-control b. kinetic control c. 1 ,4-control d. thermodynamic control |
B. kinetic control
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The geometry that allows for E2 reactions is termed?
a. syn periplanar b. anti periplanar c . square planar d. syn perpendicular e. anti perpendicular |
B. anti periplanar
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The Diels Alder reaction can be classified as which of the following types of cycloadditions?
A. 1+1 B. 2+2 C. 3+2 D. 4+2 E. 4+4 |
D. 4+2
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For Diels-Alder cycloaddition reactions to take place most rapidly and in highest yield the dienophile must:
A. be substituted with electron-withdrawing groups B. be able to adopt an s-trans conformation C. be substituted with electron-donating groups D. be able to adopt an s-cis conformation E. have less than 6 carbons |
A. be substituted with electron-withdrawing groups
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When an organic molecule is irradiated with ultraviolet radiation, the energy absorbed by the molecule
corresponds to: A. the amount necessary to increase molecular motions in functional groups B. the amount necessary to excite electrons from one molecular orbital to another C. the amount necessary to "flip" the spin of atomic nuclei D. the amount necessary to strip a molecule of one electron to generate a radical cation E. the amount necessary to break C-C bonds and fragment the molecule |
B. the amount necessary to excite electrons from one molecular orbital to another
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