Question 1

Naltrexone is an FDA-approved treatment for alcoholism that targets the mu opioid receptor.Name four functional groups that are present in naltrexone.

Accepted Answer

A) Amine, phenol, aldehyde, ether 
B) Amine, phenol, amide, alcohol 
C) Amine, phenol, ketone, alcohol 
D) Ether, ketone, amide, alcohol 
E) Ketone, phenol, alcohol, ester 
A) Amine, phenol, aldehyde, ether 
B) Amine, phenol, amide, alcohol 
C) Amine, phenol, ketone, alcohol 
D) Ether, ketone, amide, alcohol 
E) Ketone, phenol, alcohol, ester C

Question 2

In sum,how many total hydrogen atoms are directly connected to the phenyl rings found in the molecule below?

Accepted Answer

A) 8 
B) 9 
C) 10 
D) 11 
E) 12 
A) 8 
B) 9 
C) 10 
D) 11 
E) 12 C

Question 3

A carbonyl,the C   
O unit,is a component of many important functional groups.Consider the Lewis structures below.Convert the Lewis structures to line structures,showing all lone pairs.Indicate bond dipoles using the arrow method.Rank the structures for increasing partial positive charge.Predict which carbonyl carbon should have greatest partial positive charge,assuming that the chlorine lone pairs do not engage in resonance.Explain your answer.

Accepted Answer

The point of difference in the three structures is the substitution on the carbon of the carbonyl.Any property that influences electron distribution will influence the magnitude of the positive charge.Effects are either electron withdrawing (e.g.,an electronegative atom)or electron donating (e.g.,compare the Pauling electronegativity values and resonance potential of each atom).The carbonyl carbon of the acyl chloride has the greatest partial positive charge.There are three lone pairs on Cl and two on the O of the OH.Because one of the oxygen lone pairs can be delocalized through resonance,electron density is added to the C   O,and the partial positive charge of the carbonyl carbon is reduced.Given that Cl does not typically engage in resonance,then the electron withdrawing nature of the electronegative Cl predominates.

Question 4

A C-O single bond is 143 pm in length,whereas an O-O single bond is 148 pm in length. Which bond is weaker and why?

Accepted Answer

A) The C-O bond is weaker because O is more electronegative than C. 
B) The C-O bond is weaker because each O atom is electronegative and pulls the shared electrons toward itself. 
C) The O-O bond is weaker because oxygen has d orbitals to engage in bonding. 
D) The C-O bond is weaker because C is more electronegative than O. 
E) The O-O bond is weaker because both oxygens are equally electronegative and pull the shared electrons toward themselves. 
A) The C-O bond is weaker because O is more electronegative than C. 
B) The C-O bond is weaker because each O atom is electronegative and pulls the shared electrons toward itself. 
C) The O-O bond is weaker because oxygen has d orbitals to engage in bonding. 
D) The C-O bond is weaker because C is more electronegative than O. 
E) The O-O bond is weaker because both oxygens are equally electronegative and pull the shared electrons toward themselves.

Question 5

Tubulysin D is a potent cytotoxic compound that interferes with mitosis.Identify the following structural features of Tubulysin D.
(a)Place a box around any amide found in the molecule.
(b)Circle the phenyl group(s).
(c)Place a triangle around the carboxylic acid(s).
(d)Star any carbon atoms with a -3 oxidation state.

Accepted Answer

@#IMG-DLM& * = Oxida

Question 6

Identify which carbon atom in the molecule below is most oxidized.

Accepted Answer

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

Question 7

Consider the interesting structure below,called a dibromocarbene.The carbon of the dibromocarbene has one lone electron pair and two separate covalent bonds to individual bromine atoms.What is the formal charge on the carbon atom of the dibromocarbene?

Accepted Answer

A) +2 
B) +1 
C) 0 
D) -1 
E) -2 
A) +2 
B) +1 
C) 0 
D) -1 
E) -2

Question 8

To which carbon atoms in anisole would a positively charged species,called "E+," bond? Explain your answer using the concept of resonance.HINT: Refer to your response from 16 for further insight.

Accepted Answer

Opposites attract.It is reasonable to pr

Question 9

Which would you expect to be a stronger bond: C-Si or C-C?

Accepted Answer

A C-Si single bond is weaker and longer

Question 10

The way atoms are connected to each other in an organic structure determines the chemical behavior of the structure.Using line structures,propose individual molecules with the formula C4H8O that contain the following functional groups:
(a)A ketone (e)A cyclic ether that is not an epoxide
(b)An aldehyde with a branched alkane (f)An epoxide
(c)An aldehyde with an unbranched alkane (g)An acyclic ether
(d)A cycloalkane (h)An alkene and an alcohol

Accepted Answer

Question 11

Which electron configuration is correct for the carbon of a carbocation?

Accepted Answer

A) 1s22s22p1 
B) 1s22s22p3 
C) 1s22s22p5 
D) 1s22s22p63s23p5 
E) 1s22s22p4 
A) 1s22s22p1 
B) 1s22s22p3 
C) 1s22s22p5 
D) 1s22s22p63s23p5 
E) 1s22s22p4

Question 12

Which of the following is an example of an electrostatic attractive force between particles at the atomic level?

Accepted Answer

A) Neutrons attract protons. 
B) Protons repel protons. 
C) Core electrons attract valence electrons. 
D) Protons attract electrons. 
E) Electrons attract neutrons. 
A) Neutrons attract protons. 
B) Protons repel protons. 
C) Core electrons attract valence electrons. 
D) Protons attract electrons. 
E) Electrons attract neutrons.

Question 13

Consider two solvents that are commonly used for organic chemistry reactions: CH2Cl2 and CCl4.Interestingly,studies have shown that one of these solvents is polar and one is nonpolar.Draw valid Lewis structures for these two molecules.Show bond dipoles and both partial charges (use δ+ and δ-).How would the electrostatic potential maps for the two molecules be similar? How would they be different?

Accepted Answer

Although CCl₄ has individual bond dipoles

Question 14

Which point on the following diagram represents two atoms functioning independently?  
)

Accepted Answer

A) A 
B) B 
C) C 
D) D 
E) E 
A) A 
B) B 
C) C 
D) D 
E) E

Question 15

Draw a Lewis structure of thionyl chloride,SOCl2,showing all lone pairs.Show each bond dipole using a dipole arrow.

Accepted Answer

Question 16

How many valence electrons are assigned to oxygen when determining formal charge in the ionic compound sodium methoxide,NaOCH3?

Accepted Answer

A) 4 
B) 5 
C) 6 
D) 7 
E) 8 
A) 4 
B) 5 
C) 6 
D) 7 
E) 8

Question 17

Predict which carbon atom should have the greatest negative charge density.Explain your answer.What would the electrostatic potential map show for this carbon,in comparison with others in the molecule?

Accepted Answer

@#IMG-DLM& The electrostatic potential map for the

Question 18

Which electron configuration is correct for a Ca2+ ion?

Accepted Answer

A) 1s22s22p63s23p1 
B) 1s22s22p63s23p64s2 
C) 1s22s22p63s23p6 
D) 1s22s22p63s23p64s24p6 
E) 1s22s22p63s2 
A) 1s22s22p63s23p1 
B) 1s22s22p63s23p64s2 
C) 1s22s22p63s23p6 
D) 1s22s22p63s23p64s24p6 
E) 1s22s22p63s2

Question 19

A compound with a molecular formula of C7H7Br has a melting point of 203°C.The compound is soluble in water but not in diethyl ether.Based on your knowledge of organic structure,is the compound most stable in its ionic or covalent form? Justify your answer.

Accepted Answer

The high melting point of +200 degrees a

Question 20

For which of the following F1F1F1S1F1F1F10amino acids can resonance forms be drawn for its side chain?

Accepted Answer

A) Alanine 
B) Methionine 
C) Glycine 
D) Proline 
E) Histidine 
A) Alanine 
B) Methionine 
C) Glycine 
D) Proline 
E) Histidine

Exam 1: Atomic and Molecular Structure

Naltrexone is an FDA-approved treatment for alcoholism that targets the mu opioid receptor.Name four functional groups that are present in naltrexone.

In sum,how many total hydrogen atoms are directly connected to the phenyl rings found in the molecule below?

A C-O single bond is 143 pm in length,whereas an O-O single bond is 148 pm in length. Which bond is weaker and why?

Identify which carbon atom in the molecule below is most oxidized.

Consider the interesting structure below,called a dibromocarbene.The carbon of the dibromocarbene has one lone electron pair and two separate covalent bonds to individual bromine atoms.What is the formal charge on the carbon atom of the dibromocarbene?

To which carbon atoms in anisole would a positively charged species,called "E+," bond? Explain your answer using the concept of resonance.HINT: Refer to your response from 16 for further insight.

Which would you expect to be a stronger bond: C-Si or C-C?

Which electron configuration is correct for the carbon of a carbocation?

Which of the following is an example of an electrostatic attractive force between particles at the atomic level?

Which point on the following diagram represents two atoms functioning independently? )

Draw a Lewis structure of thionyl chloride,SOCl2,showing all lone pairs.Show each bond dipole using a dipole arrow.

How many valence electrons are assigned to oxygen when determining formal charge in the ionic compound sodium methoxide,NaOCH3?

Predict which carbon atom should have the greatest negative charge density.Explain your answer.What would the electrostatic potential map show for this carbon,in comparison with others in the molecule?

Which electron configuration is correct for a Ca2+ ion?

A compound with a molecular formula of C7H7Br has a melting point of 203°C.The compound is soluble in water but not in diethyl ether.Based on your knowledge of organic structure,is the compound most stable in its ionic or covalent form? Justify your answer.

For which of the following amino acids can resonance forms be drawn for its side chain?

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 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

To which carbon atoms in anisole would a positively charged species,called "E⁺," bond? Explain your answer using the concept of resonance.HINT: Refer to your response from 16 for further insight.

Draw a Lewis structure of thionyl chloride,SOCl₂,showing all lone pairs.Show each bond dipole using a dipole arrow.

How many valence electrons are assigned to oxygen when determining formal charge in the ionic compound sodium methoxide,NaOCH₃?

Which electron configuration is correct for a Ca²⁺ ion?

A compound with a molecular formula of C₇H₇Br has a melting point of 203°C.The compound is soluble in water but not in diethyl ether.Based on your knowledge of organic structure,is the compound most stable in its ionic or covalent form? Justify your answer.