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Exam 8: The Proton Transfer Reaction: an Introduction to Mechanisms,thermodynamics,and Charge Stability

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Exam 1: Atomic and Molecular Structure54 Questionsadd course
Exam 2: Interchapter: Nomenclature 1-477 Questionsadd course
Exam 3: Interchapter 1molecular Orbital Theory and Chemical Reactions17 Questionsadd course
Exam 4: Three-Dimensional Geometry,intermolecular Interactions,and Physical Properties53 Questionsadd course
Exam 5: Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals56 Questionsadd course
Exam 6: Isomerism 1: Conformational and Constitutional Isomers60 Questionsadd course
Exam 7: Isomerism 2: Chirality,enantiomers,and Diastereomers63 Questionsadd course
Exam 8: The Proton Transfer Reaction: an Introduction to Mechanisms,thermodynamics,and Charge Stability51 Questionsadd course
Exam 9: An Overview of the Most Common Elementary Steps58 Questionsadd course
Exam 10: An Introduction to Multistep Mechanisms: Sn1 and E1 Reactions59 Questionsadd course
Exam 11: Nucleophilic Substitution and Elimination Reactions 1: Competition Among Sn2,sn1,e2,and E1 Reactions50 Questionsadd course
Exam 12: Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis58 Questionsadd course
Exam 13: Electrophilic Addition to Nonpolar Π Bonds 1: Addition of a Brønsted Acid50 Questionsadd course
Exam 14: Electrophilic Addition to Nonpolar Π Bonds 2: Reactions Involving Cyclic Transition States55 Questionsadd course
Exam 15: Organic Synthesis 1: Beginning Concepts50 Questionsadd course
Exam 16: Orbital Interactions 2: Extended Π Systems,conjugation,and Aromaticity54 Questionsadd course
Exam 17: Structure Determination 1: Ultravioletvisible and Infrared Spectroscopies50 Questionsadd course
Exam 18: Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry60 Questionsadd course
Exam 19: Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles50 Questionsadd course
Exam 20: Nucleophilic Addition to Polar Π Bonds 2: Addition of Weak Nucleophiles and Acid and Base Catalysis63 Questionsadd course
Exam 21: Organic Synthesis 2: Intermediate Topics in Synthesis Design,and Useful Reduction and Oxidation Reactions50 Questionsadd course
Exam 22: Nucleophilic Additionelimination Reactions 1: the General Mechanism Involving Strong Nucleophiles55 Questionsadd course
Exam 23: Nucleophilic Additionelimination Reactions 2: Weak Nucleophiles54 Questionsadd course
Exam 24: Electrophilic Aromatic Substitution 1: Substitution on Benzene; Useful Accompanying Reactions50 Questionsadd course
Exam 25: Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings50 Questionsadd course
Exam 26: The Dielsalder Reaction and Other Pericyclic Reactions53 Questionsadd course
Exam 27: Reactions Involving Free Radicals50 Questionsadd course
Exam 28: Polymers51 Questionsadd course
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Explain why hydrogen atoms attached to sp2 carbons are more acidic than hydrogen atoms attached to sp3 carbons.

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Question 1
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Sp2 carbons are more electronegative than sp3 carbons; thus,after deprotonation,they can better handle having a negative charge.Therefore,hydrogens attached to sp2 carbons are more acidic.

Which of the compounds is most acidic? Which of the compounds is most acidic?

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Question 2
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A

Which of the following compounds is most acidic? Which of the following compounds is most acidic?

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Question 3
Correct Answer:
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C

Suppose the following molecules undergo a proton transfer reaction.Draw the mechanism and give the most likely products.Be sure to include all mechanism arrows,electron pairs,and formal charges for all starting materials and products. Suppose the following molecules undergo a proton transfer reaction.Draw the mechanism and give the most likely products.Be sure to include all mechanism arrows,electron pairs,and formal charges for all starting materials and products.

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Question 4

Which of the following compounds is most basic? Which of the following compounds is most basic?

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Question 5

What is the correct proton transfer mechanism for the following reaction? What is the correct proton transfer mechanism for the following reaction?

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Question 6

Rank the following carbocations in order of most stable to least stable. Rank the following carbocations in order of most stable to least stable.

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Question 7

Supply the conjugate acid for the following base. Supply the conjugate acid for the following base.

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Question 8

Which of the following protons has the lowest pKa? Which of the following protons has the lowest pKa?

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Question 9

Which of the following resonance structures contributes most to the resonance hybrid? Which of the following resonance structures contributes most to the resonance hybrid?

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Question 10

Explain why Compound A is more acidic than Compound B.Use resonance structures to explain your answer. Explain why Compound A is more acidic than Compound B.Use resonance structures to explain your answer.

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Question 11

Rank the acidity of the following compounds in order of most acidic to least acidic. Rank the acidity of the following compounds in order of most acidic to least acidic.

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Question 12

Rank the following compounds in order of most basic to least basic. Rank the following compounds in order of most basic to least basic.

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Question 13

Supply the conjugate base for the following acid. Supply the conjugate base for the following acid.

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Question 14

Draw all the resonance structures for the following compound,and determine which contributes most to the resonance hybrid. Draw all the resonance structures for the following compound,and determine which contributes most to the resonance hybrid.

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Question 15

Which of the following is least basic? Which of the following is least basic?

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Question 16

Which of the hydrogen atoms is most acidic? Which of the hydrogen atoms is most acidic?

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Question 17

Rank the acidity of the following compounds in order of most acidic to least acidic. Rank the acidity of the following compounds in order of most acidic to least acidic.

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Question 18

Give the Keq expression for the following reaction. Give the K<sub>eq</sub> expression for the following reaction.

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Question 19

Draw the mechanism for the following proton transfer reaction.Be sure your mechanism includes all mechanism arrows,lone pairs,and formal charges.Also,supply a free energy diagram.On the diagram,label the transition state,ΔG0‡,and ΔG0rxn. Draw the mechanism for the following proton transfer reaction.Be sure your mechanism includes all mechanism arrows,lone pairs,and formal charges.Also,supply a free energy diagram.On the diagram,label the transition state,ΔG<sup>0‡</sup>,and ΔG<sup>0</sup><sub>rxn</sub>.

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