Question 1

Which molecule represents the chair-flipped conformer of the given compound?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 2

What is the IHD for the formula C8H17NOClF?

Accepted Answer

Question 3

The Newman projection looking down the indicated bond in the species below is best represented by which of the following (I,II,III,IV,or V)?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 4

Which is the least stable cyclohexane conformation?

Accepted Answer

A) Chair 
B) Half-chair 
C) Twist-boat 
D) Boat 
E) Crown 
A) Chair 
B) Half-chair 
C) Twist-boat 
D) Boat 
E) Crown

Question 5

Which set of molecules are not considered constitutional isomers?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 6

Rank the steric strain of the following types of conformations from highest energy to lowest energy.

Accepted Answer

A) Anti > eclipsed > gauche 
B) Eclipsed > anti > gauche 
C) Gauche > anti > eclipsed 
D) Eclipsed > gauche > anti 
A) Anti > eclipsed > gauche 
B) Eclipsed > anti > gauche 
C) Gauche > anti > eclipsed 
D) Eclipsed > gauche > anti

Question 7

Which of the following pairs do not have the same connectivity?

Accepted Answer

A) Two stereoisomers 
B) Two conformational isomers 
C) Cyclohexane chair conformations before and after a chair flip 
D) Two constitutional isomers 
E) Two Newman projection rotamers 
A) Two stereoisomers 
B) Two conformational isomers 
C) Cyclohexane chair conformations before and after a chair flip 
D) Two constitutional isomers 
E) Two Newman projection rotamers

Question 8

Calculate the index of hydrogen deficiency for the following formula: C8H12NOF2-.

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 4 
A) 0 
B) 1 
C) 2 
D) 3 
E) 4

Question 9

Draw the Newman projection for the following species.

Accepted Answer

The answer of Draw the Newman projection for the following...

Question 10

Which structure best represents the following disubstituted cyclohexane?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 11

Which conformer is highest in energy?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 12

Which Newman projection results from rotating the front carbon 240° clockwise?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 13

Would the cis or trans isomer be more stable for the following disubstituted cyclohexane? Explain.

Accepted Answer

The cis isomer would be more s

Question 14

Which Haworth projection corresponds to the following chair conformation?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 15

The Newman projection looking down the indicated bond in the species below is best represented by which of the following (I,II,III,IV,or V)?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 16

Which of the following isomers is most stable?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) I, II, and III have the same stability and are more stable than IV. 
A) I 
B) II 
C) III 
D) IV 
E) I, II, and III have the same stability and are more stable than IV.

Question 17

Perform a conformational analysis of 1,1-dichloropropane looking down the C1F1F1F1S1F1F1F10C2 bond.

Accepted Answer

The answer of Perform a conformational analysis of 1,1-dichloropropane looking...

Question 18

Which of the following molecules has the largest molar heat of combustion?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 19

Which set of molecules does not consist of constitutional isomers?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) V 
A) I 
B) II 
C) III 
D) IV 
E) V

Question 20

Explain why cyclohexane has less ring strain than cyclopropane.

Accepted Answer

The preferred angle for sp³-hyb

Exam 6: Isomerism 1: Conformational and Constitutional Isomers

Which molecule represents the chair-flipped conformer of the given compound?

What is the IHD for the formula C8H17NOClF?

The Newman projection looking down the indicated bond in the species below is best represented by which of the following (I,II,III,IV,or V)?

Which is the least stable cyclohexane conformation?

Which set of molecules are not considered constitutional isomers?

Rank the steric strain of the following types of conformations from highest energy to lowest energy.

Which of the following pairs do not have the same connectivity?

Calculate the index of hydrogen deficiency for the following formula: C8H12NOF2-.

Draw the Newman projection for the following species.

Which structure best represents the following disubstituted cyclohexane?

Which conformer is highest in energy?

Which Newman projection results from rotating the front carbon 240° clockwise?

Would the cis or trans isomer be more stable for the following disubstituted cyclohexane? Explain.

Which Haworth projection corresponds to the following chair conformation?

The Newman projection looking down the indicated bond in the species below is best represented by which of the following (I,II,III,IV,or V)?

Which of the following isomers is most stable?

Perform a conformational analysis of 1,1-dichloropropane looking down the C1C2 bond.

Which of the following molecules has the largest molar heat of combustion?

Which set of molecules does not consist of constitutional isomers?

Explain why cyclohexane has less ring strain than cyclopropane.

Atomic and Molecular Structure

Interchapter: Nomenclature 1-4

Interchapter 1molecular Orbital Theory and Chemical Reactions

Three-Dimensional Geometry,intermolecular Interactions,and Physical Properties

Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Isomerism 2: Chirality,enantiomers,and Diastereomers

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

An Overview of the Most Common Elementary Steps

An Introduction to Multistep Mechanisms: Sn1 and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 1: Competition Among Sn2,sn1,e2,and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis

Electrophilic Addition to Nonpolar Π Bonds 1: Addition of a Brønsted Acid

Electrophilic Addition to Nonpolar Π Bonds 2: Reactions Involving Cyclic Transition States

Organic Synthesis 1: Beginning Concepts

Orbital Interactions 2: Extended Π Systems,conjugation,and Aromaticity

Structure Determination 1: Ultravioletvisible and Infrared Spectroscopies

Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

Nucleophilic Addition to Polar Π Bonds 2: Addition of Weak Nucleophiles and Acid and Base Catalysis

Organic Synthesis 2: Intermediate Topics in Synthesis Design,and Useful Reduction and Oxidation Reactions

Nucleophilic Additionelimination Reactions 1: the General Mechanism Involving Strong Nucleophiles

Nucleophilic Additionelimination Reactions 2: Weak Nucleophiles

Electrophilic Aromatic Substitution 1: Substitution on Benzene; Useful Accompanying Reactions

Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings

The Dielsalder Reaction and Other Pericyclic Reactions

Reactions Involving Free Radicals

Polymers

Filters

What is the IHD for the formula C₈H₁₇NOClF?

Calculate the index of hydrogen deficiency for the following formula: C₈H₁₂NOF₂^-.