Podcast
Questions and Answers
Which of the following is (2S,3R)-2,3-dihydroxybutanal?
Which of the following is (2S,3R)-2,3-dihydroxybutanal?
- Compound I and II
- Compound II
- Compound I
- Compound III (correct)
What is the percentage composition of enantiomers in the given mixture with an observed specific rotation of +11.2?
What is the percentage composition of enantiomers in the given mixture with an observed specific rotation of +11.2?
- 60% (R), 40% (S)
- 40% (R), 60% (S)
- 64% (R), 36% (S) (correct)
- 36% (R), 64% (S)
What type of isomers are molecules I and II?
What type of isomers are molecules I and II?
- Constitutional isomers (correct)
- Identical
- Diastereomers
- Enantiomers
Which of the following pairs are enantiomers?
Which of the following pairs are enantiomers?
Which statements about 1,1-dicyclopentanyl ethane are correct?
Which statements about 1,1-dicyclopentanyl ethane are correct?
What is the IUPAC name for the compound represented?
What is the IUPAC name for the compound represented?
How many stereoisomers can be drawn for 3,3,5-trimethylhept-1-en-6-yne?
How many stereoisomers can be drawn for 3,3,5-trimethylhept-1-en-6-yne?
What is the IUPAC name of the given compound?
What is the IUPAC name of the given compound?
Which of the following compounds is a meso compound?
Which of the following compounds is a meso compound?
Which statement about the SN1 mechanism is incorrect?
Which statement about the SN1 mechanism is incorrect?
Which feature distinguishes constitutional isomers from other types of isomers?
Which feature distinguishes constitutional isomers from other types of isomers?
What is necessary for a compound to be classified as enantiomers?
What is necessary for a compound to be classified as enantiomers?
What is the initial rate of the reaction given k = 2.0 x 10^-2 M^-1s^-1, [CH3Br] = 0.2 M, and [OH-] = 0.5 M?
What is the initial rate of the reaction given k = 2.0 x 10^-2 M^-1s^-1, [CH3Br] = 0.2 M, and [OH-] = 0.5 M?
Which of the following molecules is NOT likely to be chiral?
Which of the following molecules is NOT likely to be chiral?
In molecular structure representation, what designates a molecule as diastereomers?
In molecular structure representation, what designates a molecule as diastereomers?
In which scenario do nucleophilicities not parallel basicities?
In which scenario do nucleophilicities not parallel basicities?
Which statement about the nucleophiles I − and F − is correct in different solvent types?
Which statement about the nucleophiles I − and F − is correct in different solvent types?
What is the correct order of leaving group ability in nucleophilic substitution reactions?
What is the correct order of leaving group ability in nucleophilic substitution reactions?
Which compound arrangement depicts the correct order of increasing SN1 reaction rates?
Which compound arrangement depicts the correct order of increasing SN1 reaction rates?
Which solvent favors an SN1 reaction over SN2?
Which solvent favors an SN1 reaction over SN2?
What is the order of increasing SN2 reaction rates for the given compounds?
What is the order of increasing SN2 reaction rates for the given compounds?
Which solvent would likely yield the fastest reaction rate for nucleophilic substitution?
Which solvent would likely yield the fastest reaction rate for nucleophilic substitution?
Which statement correctly describes the relationship between solvent type and the SN2 mechanism?
Which statement correctly describes the relationship between solvent type and the SN2 mechanism?
Flashcards
Constitutional Isomers
Constitutional Isomers
Molecules with the same molecular formula but different structural arrangements.
Enantiomers
Enantiomers
Non-superimposable mirror images of each other.
Diastereomers
Diastereomers
Stereoisomers that are not mirror images.
Chiral Center
Chiral Center
A carbon atom bonded to four different groups.
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Stereoisomers (3,3,5-trimethylhept-1-en-6-yne)
Stereoisomers (3,3,5-trimethylhept-1-en-6-yne)
Isomers that differ in the arrangement of atoms in space.
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Meso Compound
Meso Compound
A molecule with chiral centers but an overall achiral structure (superimposable on its mirror image).
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Stereochemical Possibilities (3,3,5-trimethylhept-1-en-6-yne)
Stereochemical Possibilities (3,3,5-trimethylhept-1-en-6-yne)
The number of possible spatial arrangements. This specific example would have a number of stereochemical possibilities.
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1,1-Dicylcopentanyl Ethane
1,1-Dicylcopentanyl Ethane
A compound potentially having a chiral center depending on its specific structure. Further information is needed to conclude whether it has a chiral center or not
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Enantiomers
Enantiomers
Molecules that are mirror images of each other but are not superimposable.
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(2S,3R)-2,3-dihydroxybutanal
(2S,3R)-2,3-dihydroxybutanal
A specific chiral molecule with designated stereochemistry at two carbon atoms, part of a class of compounds.
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Specific Rotation
Specific Rotation
A measure of the rotation of plane-polarized light by an optically active substance.
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SN1 Reaction
SN1 Reaction
A unimolecular nucleophilic substitution reaction involving a carbocation intermediate.
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SN2 Reaction
SN2 Reaction
A bimolecular nucleophilic substitution reaction occurring in a single step.
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IUPAC name
IUPAC name
The systematic naming of a chemical compound according to a set of rules.
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Rate Constant
Rate Constant
A proportionality constant that quantifies how quickly a chemical reaction proceeds.
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Chirality
Chirality
A property of a molecule that lacks reflection symmetry.
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Nucleophile-basicity relationship
Nucleophile-basicity relationship
Nucleophilicity (ability to donate electrons) often parallels basicity (ability to accept protons) for nucleophiles with the same atom. However, this generally isn't true when nucleophiles have different atoms.
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Nucleophile strength in protic solvent
Nucleophile strength in protic solvent
Nucleophiles in protic solvents (like water or alcohol) often have more available electrons to share because they don't become heavily associated with the solvent.
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Nucleophile strength in aprotic solvent
Nucleophile strength in aprotic solvent
Nucleophiles in aprotic solvents (without readily accepting protons, like acetone) can be strongly affected by charge interactions. This can lead to differences in nucleophilicity compared to basicity
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Leaving group ability order
Leaving group ability order
The ability of a group to leave a molecule in nucleophilic substitution reactions, Br⁻ > Cl⁻ > OH⁻ > H⁻
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SN1 reaction rate factors (solvents)
SN1 reaction rate factors (solvents)
SN1 reactions, which proceed through carbocation intermediates, are favored by polar protic solvents, such as water; polar solvents help stabilize the carbocation intermediate.
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SN2 reaction rate factors (solvents)
SN2 reaction rate factors (solvents)
SN2 reactions, which proceed through a backside attack, are favored by polar aprotic solvents. These solvents don't interfere with the nucleophilic attack.
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Fastest solvent for a reaction
Fastest solvent for a reaction
The solvent which supports the fastest reaction rate depends on the specific reaction type.
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Rate factors in SN2
Rate factors in SN2
Consider factors like steric hindrance, nucleophile strength, and the leaving group ability to determine the rate of an SN2 reaction.
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Instructions for Practice Exam
- Use a pen to write your name on the scantron and the exam.
- Match the names on both.
- Answer questions 1-18 on the scantron using a pencil.
- Answer questions 19-23 on the exam sheet, with the indicated point values.
- Transfer answers to the scantron in time.
- No extra time will be given for transferring answers.
- Plagiarism will result in a 0 grade and expulsion from the exam.
- No pages may be removed from the exam.
Periodic Table Information
- A periodic table is provided, with atomic numbers, symbols, and atomic weights.
- Separate sections for lanthanide and actinide series are included.
Relative Strength of Acids and Conjugate Bases
- A table of selected acids, their approximate pKa values, and their conjugate bases are listed.
Midterm III Practice Exam Questions (Pages 2-3)
- Question 1: I and II are constitutional isomers, enantiomers, identical, diastereomers, or not isomeric.
- Question 2: 1,1-dicyclopentanyl ethane does, or does not, have a chiral center.
- Question 3: Number of stereoisomers for 3,3,5-trimethylhept-1-en-6-yne.
- Question 4: Determine which molecules are meso compounds.
- Other specific questions on various organic chemistry topics including structural formulas, isomers, chiral centers, and reactions (SN1 and SN2).
Additional Questions (Pages 4-7)
- Question 5: Identify a specific compound (2S,3R)-2,3-dihydroxybutanal.
- Question 6: Determine percentages of isomers (R and S) in a mixture given specific rotation,
- Questions 7-18: Various organic chemistry questions on molecules, reactions, and stereochemistry.
- Questions 19-23: Additional organic chemistry problems that require reactions, formulas or structures.
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