Question 1

Which of the following molecules contains a nitrogen atom with linear geometry?

Accepted Answer

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

Question 2

Which cycloalkane contains a CF1F1F1S1F1F1F10CF1F1F1S1F1F1F10F1F1F1S1F1F1F10C bond angle that deviates from the ideal tetrahedral bond angle by approximately 50°?

Accepted Answer

A) A seven-membered cycloalkane 
B) A six-membered cycloalkane 
C) A five-membered cycloalkane 
D) A four-membered cycloalkane 
E) A three-membered cycloalkane 
A) A seven-membered cycloalkane 
B) A six-membered cycloalkane 
C) A five-membered cycloalkane 
D) A four-membered cycloalkane 
E) A three-membered cycloalkane

Question 3

Sodium chloride,an ionic compound,is highly water soluble but minimally soluble in the polar aprotic solvent dimethyl sulfoxide (DMSO).Why?

Accepted Answer

Dimethyl sulfoxide possesses two methyl

Question 4

Add substituents using dash-wedge notation to achieve the structure specified.
(a) An alkene that has a fluorine atom pointing back on the leftmost carbon and a methyl group coming out on the rightmost carbon.Assume that hydrogen fills the valence of carbon.
(b) A tetrahedral carbon with two chlorine atoms pointing down on the plane of the paper,a bromine atom pointing up,and a hydrogen atom pointing back.

Accepted Answer

The answer of Add substituents using dash-wedge notation to achieve...

Question 5

Which of the following benzene derivatives would be most soluble in benzene? Why?

Accepted Answer

Adding extra benzene rings to the molecu

Question 6

What is the strongest intermolecular attractive force possible between an alkyl chloride and an alkane?

Accepted Answer

A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole 
A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole

Question 7

Rank N-N-dimethylaniline,phenethylamine,and phenethylamine hydrochloride in order of decreasing boiling point.Explain your reasoning.

Accepted Answer

The salt phenethylamine hydrochloride,a

Question 8

Which cycloalkane contains a CF1F1F1S1F1F1F10CF1F1F1S1F1F1F10F1F1F1S1F1F1F10C bond angle that deviates from the ideal tetrahedral bond angle by approximately 20°?

Accepted Answer

A) A seven-membered cycloalkane 
B) A six-membered cycloalkane 
C) A five-membered cycloalkane 
D) A four-membered cycloalkane 
E) A three-membered cycloalkane 
A) A seven-membered cycloalkane 
B) A six-membered cycloalkane 
C) A five-membered cycloalkane 
D) A four-membered cycloalkane 
E) A three-membered cycloalkane

Question 9

The solvent tert-butyl methyl ether (MTBE)is used as a "greener" replacement for the organic solvent diethyl ether,because it has less propensity to form peroxides upon standing.Draw the line structures of both diethyl ether and MTBE.Look up the physical properties (boiling point,flash point)of both solvents.Explain why the boiling point of diethyl ether is lower.

Accepted Answer

Diethyl ether has a smaller mo

Question 10

What is the VSEPR geometry for any carbon atom in a phenyl ring?

Accepted Answer

A) Linear 
B) Tetrahedral 
C) Trigonal pyramidal 
D) Trigonal planar 
E) Bent 
A) Linear 
B) Tetrahedral 
C) Trigonal pyramidal 
D) Trigonal planar 
E) Bent

Question 11

Which of the following intermolecular forces is responsible for the boiling-point trends in alkanes?

Accepted Answer

A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole 
A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole

Question 12

Propanol can be dissolved in diethyl ether and treated with sodium hydride,a base,to form a sodium alkoxide,as shown below.   
Although this and related chemical reactions will be studied in later chapters,you can apply your knowledge of solubility to the process.
Fill in your solubility predictions using the table below.Do you expect propanol (I),sodium propoxide (II),and the new ether product (III)to be soluble in the reaction solvent,diethyl ether? If soluble,predict the intermolecular interactions that will exist in solution.Also,anticipate the physical appearance of the reaction at each point: Will the solution be transparent,or will a precipitate form?

Accepted Answer

The answer of Propanol can be dissolved in diethyl ether...

Question 13

Tertiary amides are typically insoluble in water.The solvent dimethyl acetamide,CH3CON(CH3)2,which is commonly called DMA,is an exception.Explain why the solvent DMA is soluble in water.Diagram the intermolecular forces that make DMA soluble in water.

Accepted Answer

Question 14

Which of the following choices correctly describes the structure of the ball-and-stick representation with the formula H3C+?

Accepted Answer

A) A carbocation with a tetrahedral carbon 
B) A carbocation with trigonal planar geometry 
C) A carbocation with unknown geometry 
D) A carbanion with a tetrahedral carbon 
E) A carbanion with trigonal planar geometry 
A) A carbocation with a tetrahedral carbon 
B) A carbocation with trigonal planar geometry 
C) A carbocation with unknown geometry 
D) A carbanion with a tetrahedral carbon 
E) A carbanion with trigonal planar geometry

Question 15

Which of the following molecules contains a trigonal planar nitrogen atom connected to two different tetrahedral carbon atoms?

Accepted Answer

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

Question 16

Your lab partner disobeyed lab rules and poured table salt from lunch into your unknown organic white powder,which is aprotic and contains an ester functional group.What solvent might you add to the solid mixture to remove the table salt,leaving the ester? What solvent is appropriate to remove the unknown ester,leaving instead the salt? Explain your reasoning.

Accepted Answer

The basic premise of "like dissolves lik

Question 17

Identify the weakest intermolecular force.

Accepted Answer

A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole 
A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole

Question 18

When applying VSEPR theory to determine the geometry about a central atom,it is important to count the total number of bonded and nonbonded electron groups.Separately consider the two atoms highlighted with an arrow in the molecule shown below.How many bonded electron groups must be considered for each of these central atoms?

Accepted Answer

A) C has two groups; O has two groups. 
B) C has three groups; O has four groups. 
C) C has three groups; O has two groups. 
D) C has three groups; O has three groups. 
E) C has four groups; O has four groups. 
A) C has two groups; O has two groups. 
B) C has three groups; O has four groups. 
C) C has three groups; O has two groups. 
D) C has three groups; O has three groups. 
E) C has four groups; O has four groups.

Question 19

Identify the strongest intermolecular force.

Accepted Answer

A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole 
A) Hydrogen bond 
B) Ion-dipole 
C) Ion-ion 
D) Dipole-induced dipole 
E) Induced dipole-induced dipole

Question 20

Turn the original molecule shown below 90° in a clockwise direction on the plane of this paper.Which choice represents the product of this manipulation?

Accepted Answer

A) Structure a 
B) Structure b 
C) Structure c 
D) Structure d 
E) Structure e 
A) Structure a 
B) Structure b 
C) Structure c 
D) Structure d 
E) Structure e

Exam 4: Three-Dimensional Geometry,intermolecular Interactions,and Physical Properties

Which of the following molecules contains a nitrogen atom with linear geometry?

Which cycloalkane contains a CCC bond angle that deviates from the ideal tetrahedral bond angle by approximately 50°?

Sodium chloride,an ionic compound,is highly water soluble but minimally soluble in the polar aprotic solvent dimethyl sulfoxide (DMSO).Why?

Which of the following benzene derivatives would be most soluble in benzene? Why?

What is the strongest intermolecular attractive force possible between an alkyl chloride and an alkane?

Rank N-N-dimethylaniline,phenethylamine,and phenethylamine hydrochloride in order of decreasing boiling point.Explain your reasoning.

Which cycloalkane contains a CCC bond angle that deviates from the ideal tetrahedral bond angle by approximately 20°?

What is the VSEPR geometry for any carbon atom in a phenyl ring?

Which of the following intermolecular forces is responsible for the boiling-point trends in alkanes?

Tertiary amides are typically insoluble in water.The solvent dimethyl acetamide,CH3CON(CH3)2,which is commonly called DMA,is an exception.Explain why the solvent DMA is soluble in water.Diagram the intermolecular forces that make DMA soluble in water.

Which of the following choices correctly describes the structure of the ball-and-stick representation with the formula H3C+?

Which of the following molecules contains a trigonal planar nitrogen atom connected to two different tetrahedral carbon atoms?

Identify the weakest intermolecular force.

Identify the strongest intermolecular force.

Turn the original molecule shown below 90° in a clockwise direction on the plane of this paper.Which choice represents the product of this manipulation?

Atomic and Molecular Structure

Interchapter: Nomenclature 1-4

Interchapter 1molecular Orbital Theory and Chemical Reactions

Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Isomerism 1: Conformational and Constitutional Isomers

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

Tertiary amides are typically insoluble in water.The solvent dimethyl acetamide,CH₃CON(CH₃)₂,which is commonly called DMA,is an exception.Explain why the solvent DMA is soluble in water.Diagram the intermolecular forces that make DMA soluble in water.

Which of the following choices correctly describes the structure of the ball-and-stick representation with the formula H₃C⁺?