Orgo midterm

smith 1-7

What is the ground-state electronic configuration of a carbon atom?

B) 1s2,2s2,2p2

What is the ground-state electronic configuration of a fluorine atom?

D) 1s2, 2s2, 2p5

What is the ground-state electronic configuration of a magnesium cation (Mg2+)?

A) 1s2, 2s2, 2p6

What is the ground-state electronic configuration of a chlorine anion (Cl—)?

B) 1s2, 2s2, 2p6, 3s2,3p6

Which of the following statements about valence electrons is true?

A) They are the most tightly held electrons.

B) They do not participate in chemical reactions.

C) They are the outermost electrons.

D) They reveal the period number of a second-row element.

C) They are the outermost electrons.

Which of the following statements about bonding is true?

\
A) Covalent bonds result from the transfer of electrons from one element to another.

B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.

C) Ionic bonds result from the sharing of electrons between two nonmetals.

D) Covalent bonds result from the sharing of electrons between two metals.

B) Ionic bonds result from the transfer of electrons from a metal to a non-metal.

Which of the following would you expect to have ionic bonds?

\
A) CO

B) FBr

C) NF3

D) NaCl

D) NaCl

Which of the following molecules has nonpolar covalent bonds?

\
A) HCl

B) N2

C) CHCl3

D) NO

B) N2

Which of the following molecules contain both covalent and ionic bonds?

\
A) I, II

B) I, IV

C) II, III

D) II, IV

D) II, IV

Which of the following would most likely form an ionic bond?

\
A) I

B) II

C) III

D) IV

D) IV

Which of the following statements correctly describes the typical number of bonds for carbon, nitrogen, and oxygen in most neutral organic molecules?

\
A) Carbon forms 4 covalent bonds, nitrogen forms 2 covalent bonds and oxygen forms 3 covalent bonds.

B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds and oxygen forms 2 covalent bonds.

C) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 2 covalent bonds.

D) Carbon forms 4 covalent bonds, nitrogen forms 5 covalent bonds and oxygen forms 4 covalent bonds.

B) Carbon forms 4 covalent bonds, nitrogen forms 3 covalent bonds and oxygen forms 2 covalent bonds.

Which is not an acceptable Lewis structure for the anion CH2NCO—?

\
A) I

B) II

C) III

D) IV

C) III

Which of the following Lewis structures is drawn correctly?

\
A) I

B) II

C) III

D) IV

D) IV

Which of the following Lewis structures is correct?

\
A) I, II

B) I, III

C) II, III

D) III, IV

C) II, III

Which is the correct Lewis structure for acetic acid (CH3CO2H)?

\
A) I

B) II

C) III

D) IV

D) IV

In which of the following ions does carbon have a formal charge?

\
A) I

B) II

C) III

D) None of the above

D) None of the above

In which of the following ions does carbon have a formal charge?

\
A) I

B) II

C) III

D) None of the above

B) II

What is the formal charge of carbon in carbon monoxide (CO) when drawn with a triple bond?

\
A) 0

B) -2

C) -1

D) +1

C) -1

Which of the following statements about constitutional isomers is true?

A) Constitutional isomers are different molecules having different molecular formula.

B) Constitutional isomers are different molecules having same molecular formula.

C) Constitutional isomers are same molecules having different molecular formula.

D) Constitutional isomers are same molecules having the same molecular formula.

B) Constitutional isomers are different molecules having same molecular formula.

How many constitutional isomers are there for a molecule having the molecular formula C2H6O?

\
A) 1

B) 2

C) 3

D) 4

B) 2

How many constitutional isomers are there for a molecule having the molecular formula C3H8O?

\
A) 1

B) 2

C) 3

D) 4

C) 3

How many constitutional isomers are there for a molecule having the molecular formula C3H6?

\
A) 1

B) 2

C) 3

D) 4

B) 2

How many constitutional isomers are there for a molecule having the molecular formula C2H4Cl2?

\
A) 1

B) 2

C) 3

D) 4

B) 2

How many different consitutional isomers are there for a compound having the molecular formula C3H6O?

\
A) 4

B) 5

C) 6

D) 7

D) 7

Which of the following molecules are constitutional isomers?

\
A) I, II, IV

B) II, III, IV

C) I, III, IV

D) I, II, III

D) I, II, III

Which of the following compounds has an atom with an unfilled valence shell of electrons?

\
A) H2O

B) BCl3

C) CH4

D) CO2

B) BCl3

Which of the following statements about resonance structures is true?

\
A) Resonance structures have the same placement of electrons but different arrangement of atoms.

B) Resonance structures have the same placement of atoms but different arrangement \\n of electrons.

C) Resonance structures have the same placement of atoms and the same arrangement of electrons.

D) Resonance structures have different placement of atoms and different arrangement of electrons.

B) Resonance structures have the same placement of atoms but different arrangement of electrons.

Which of the following statements about resonance structures is not true?

A) There is no movement of electrons from one form to another.

B) Resonance structures are not isomers.

C) Resonance structures differ only in the arrangement of electrons.

D) Resonance structures are in equilibrium with each other.

A) There is no movement of electrons from one form to another.

Which of the following pair does not represent resonance structures?

\
A) I

B) II

C) III

D) IV

C) III

What 2 things will change between two resonance structures?

\
A) The position of multiple bonds and non-bonded electrons.

B) The position of multiple bonds and single bonds.

C) The placement of atoms and single bonds.

D) The placement of atoms and non-bonded electrons.

A) The position of multiple bonds and non-bonded electrons.

Which of the following is a resonance structure of the compound below?

\
A) I

B) II

C) III

D) IV

D) IV

Which of the following resonance structures is the least important contributor to the resonance hybrid of the formate anion, HCOO—?

\
A) I

B) II

C) III

D) IV

B) II

Rank the following in order of decreasing importance as contributing structures to the resonance hybrid of formaldehyde, H2CO.

\
A) I > II > III

B) I > III > II

C) II > I > III

D) III > II > I

A) I > II > III

Follow the curved arrows to draw the second resonance structure for the ion below.

\
A) I

B) II

C) III

D) IV

C) III

Which is more important in each pair of contributing resonance structures?

\
A) II, IV, V

B) II, III, V

C) II, III, VI

D) I, IV, V

B) II, III, V

What is the approximate value of the H-C-H bond angle in methane, CH4?

\
A) 90°

B) 109.5°

C) 120°

D) 180°

B) 109.5°

What is the approximate C-C-C bond angle in propene, CH3CH = CH2?

\
A) 90°

B) 109.5°

C) 120°

D) 180°

C) 120°

What is the approximate H-C-O bond angle in formaldehyde, H2CO?

\
A) 90°

B) 109.5°

C) 120°

D) 180°

C) 120°

Determine the geometry around the indicated atom in each species.

\
A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral

B) I = Linear; II = tetrahedral; III = trigonal planar; IV = linear

C) I = Trigonal planar; II = linear; III = tetrahedral; IV = trigonal planar

D) I = Tetrahedral; II = trigonal planar; III = linear; IV = tetrahedral

A) I = Linear; II = tetrahedral; III = trigonal planar; IV = tetrahedral

What is the approximate bond angle for the C-C-N bond in acetonitrile, CH3CN?

\
A) 90°

B) 109.5°

C) 120°

D) 180°

D) 180°

Which of the following is the appropriate conversion of the condensed structure, CH3COCH3, to a Lewis structure?

\
A) I

B) II

C) III

D) IV

B) II

Which of the following is the appropriate conversion of (CH3)2CHCH2CHClCH3 to a skeletal structure?

\
A) I

B) II

C) III

D) IV

B) II

Which of the following is the appropriate conversion of (CH3)4C to a skeletal structure?

\
A) I

B) II

C) III

D) IV

D) IV

What is the condensed formula of the compound below?

\
A) I

B) II

C) III

D) IV

A) I

Which of the following is the appropriate conversion of (CH3)2CHOCH2CH2CH2OH to a skeletal structure?

\
A) I

B) II

C) III

D) IV

D) IV

Convert the following skeletal structure to a condensed structure.

\
A) I

B) II

C) III

D) IV

A) I

Avobenzone is an active ingredient in some common sunscreens. Which of the following is the correct molecular formula for avobenzone?

\
A) C22O22O3

B) C20H22O3

C) C21H23O3

D) C20H24O3

B) C20H22O3

In which structure is the carbon hybridization incorrect?

\
A) I

B) II

C) III

D) IV

B) II

What is the hybridization for each of the indicated atoms in the following compound?

\
A) I = sp2; II = sp2; III = sp2.

B) I = sp2; II = sp3; III = sp3.

C) I = sp; II = sp2; III = sp3.

D) I = sp2; II = sp2; III = sp3.

D) I = sp2; II = sp2; III = sp3.

What is the hybridization of the carbon atom in the methyl cation, (CH3+)?

A) sp3

B) sp2

C) sp

D) p

B) sp2

What is the hybridization of the nitrogen atom in the ammonium cation, NH4+?

\
A) sp3

B) sp2

C) sp

D) p

A) sp3

Which atomic orbitals overlap to form the C-H σ bonding molecular orbitals of ethane, CH3CH3?

\
A) Csp2 + H1s

B) Csp3 + H1s

C) C2p + H1s

D) Csp + H1s

B) Csp3 + H1s

Which atomic orbitals overlap to form the C-H σ bonding molecular orbitals of ethylene, H2C=CH2?

\
A) C2p + H1s

B) Csp + H1s

C) Csp3 + H1s

D) Csp2 + H1s

D) Csp2 + H1s

Which atomic orbitals overlap to form the carbon-carbon σ and π bonding molecular orbitals of ethylene, H2C=CH2?

\
A) Csp3 + Csp3, and C2p + C2p

B) Csp3 + Csp3, and Csp2 + Csp2

C) Csp2 + Csp2, and C2p + C2p

D) Csp2 + Csp2, and Csp2 + Csp2

C) Csp2 + Csp2, and C2p + C2p

Which atomic orbitals overlap to form the C-H σ bonding molecular orbitals of acetylene, C2H2?

\
A) Csp + H1s

B) C2p +H1s

C) Csp3 + H1s

D) Csp2 + H1s

A) Csp + H1s

Which atomic orbitals overlap to form the carbon-carbon σ (sigma bonding) molecular orbital of acetylene, C2H2?

A) Csp2 + Csp2

B) Csp + Csp

C) Csp3 + Csp3

D) C2p + C2p

B) Csp + Csp

When forming molecular orbitals from atomic orbitals, what is the order of increasing C-H bond strength for the following set?

\
A) II < I < III

B) III < I < II

C) III < II < I

D) I < II < III

D) I < II < III

What is the order of decreasing bond length for a C-C bond composed of the following molecular orbitals?

\
A) I > III > II

B) I > II > III

C) III > II > I

D) II > III > I

B) I > II > III

Which of the following statements about electronegativity and the periodic table is true?

\
A) Electronegativity decreases across a row of the periodic table. B) Electronegativity increases down a column of the periodic table.

C) Electronegativity increases across a row of the periodic table.

D) Electronegativity does not change down a column of the periodic table.

C) Electronegativity increases across a row of the periodic table.

Rank the following atoms in order of increasing electronegativity, putting the least electronegative first.

\
A) I < II < III < IV

B) I < IV < II < III

C) III < II < IV < I

D) I < II < IV < III

B) I < IV < II < III

Rank the following atoms in order of decreasing electronegativity, putting the most electronegative first.

\
A) I > IV > II > III

B) II > III > IV > I

C) III > IV > II > I

D) III > II > IV > I

D) III > II > IV > I

Which molecule has the greatest difference in electronegativity (DE) between the two different elements?

\
A) CO2

B) H2S

C) NH3

D) H2O

D) H2O

Which compound contains the most polar bond?

\
A) I

B) II

C) III

D) IV

B) II

Which of the following compounds are non-polar?

\
A) I, IV

B) I, II

C) II, III

D) II, IV

A) I, IV

Which of the following molecules has non-polar covalent bonds?

\
A) CO2

B) N2

C) CCl4

D) HF

B) N2

Which of the following molecules has polar covalent bonds?

\
A) MgO

B) NH3

C) Cl2

D) NaBr

B) NH3

Which of the following covalent bonds has the largest dipole moment?

\
A) C-H

B) C-C

C) C-O

D) H-F

D) H-F

Which of the following molecules has the smallest dipole moment?

\
A) CO2

B) HCl

C) H2O

D) NH3

A) CO2

Which of the following molecules does *not* have a net dipole moment of zero?

\
A) CCl4

B) BF3

C) CO2

D) NH3

D) NH3

Which of the following molecules has a net dipole moment of zero?

\
A) I

B) II

C) III

D) IV

B) II

Consider compounds which contain both a heteroatom and a double bond. For which compound is no additional Lewis structure possible?

\
A) I

B) II

C) III

D) IV

C) III

Which of the following statements about Lewis acids is true?

\
A) Lewis acids are electron pair acceptors.

B) Lewis acids are proton donors.

C) Lewis acids are electron pair donors.

D) Lewis acids are proton acceptors.

A) Lewis acids are electron pair acceptors.

Which of the following compounds is both a Brønsted-Lowry acid and base?



A) I, II

B) I, III

C) II, IV

D) I, IV

B) I, III

What is the correct rank of the following compounds in order of decreasing acidity?

\
A) IV < III < II < I

B) II < IV < I < III

C) III < II < I < IV

D) I < II < III < IV

C) III < II < I < IV

Which of the following statements about Lewis bases is true?

\
A) Lewis bases are proton donors.

B) Lewis bases are proton acceptors.

C) Lewis bases are electron pair donors.

D) Lewis bases are electron pair acceptors.

C) Lewis bases are electron pair donors.

Rank the following compounds in order of decreasing acidity, putting the most acidic first.

\
A) IV > II > III > I

B) III > IV > II > I

C) III > IV > I > II

D) IV > III > II > I

D) IV > III > II > I

Rank the following conjugate bases in order of increasing basicity, putting the least basic first. 

\
A) I < II < III

B) II < I < III

C) I < III < II

D) II < III < I

B) II < I < III

Which of the following species cannot act as both a Brønsted-Lowry acid and base?

\
A) HSO4-

B) HCO3-

C) HO-

D) H2PO4-

C) HO-

Which of the following species is the strongest base?

\
A) HO-

B) CH3COO-

C) Cl-

D) H2N-

D) H2N-

Rank the following compounds in order of increasing acidity, putting the least acidic first. 

\
A) III < I < IV < II

B) II < I < IV < III

C) III < IV < I < II

D) III < I < II < IV

C) III < IV < I < II

Consider the following molecule with protons labeled, I-III. Rank these protons in order of decreasing acidity, putting the most acidic first.

\
A) I > II > III

B) III > II > I

C) I > III > II

D) III > I > II

B) III > II > I

Which of the following lists contains common heteroatoms found in organic molecules?

\
A) N, O, S, P, Cl

B) Na, O, S, P, Cl

C) Na, Mg, S, N, Cl

D) Na, Mg, O, N, Cl

A) N, O, S, P, Cl

Why do heteroatoms confer reactivity on a particular molecule?

\
A) Because they have lone pairs and create electron-rich sites on carbon.

B) Because they have lone pairs and create electron-deficient sites on carbon.

C) Because they are electronegative and act as electrophiles.

D) Because they are electropositive and act as nucleophiles.

B) Because they have lone pairs and create electron-deficient sites on carbon.

Why do π bonds confer reactivity on a particular molecule?

\
A) Because π bonds are difficult to break in chemical reactions.

B) Because π bonds make a molecule an acid.

C) Because π bonds are easily broken in chemical reactions.

D) Because π bonds make a molecule an electrophile.

C) Because π bonds are easily broken in chemical reactions.

Which of the following molecules contain the same functional groups?

\
A) I, II, III

B) I, II, IV

C) II, III, IV

D) I, III, IV

D) I, III, IV

Which of the following molecules contain the same functional groups?

\
A) I, II, IV

B) I, II, III

C) II, III, IV

D) I, III, IV

A) I, II, IV

Which of the following molecules are aliphatic hydrocarbons?

A) I, II, III

B) I and III

C) II, III, IV

D) II and IV

B) I and III

Which of the following molecules are aromatic hydrocarbons?

\
A) I

B) II

C) III

D) I and III

D) I and III

Which of the following correctly matches the molecules to the names of the functional group?

\
A) I and II

B) III and IV

C) II and III

D) II and IV

C) II and III

Which of the following correctly matches the molecules to the names of the functional group?

\
A) I and II

B) II and III

C) III and IV

D) I and III

D) I and III

Which of the following correctly matches the molecules to the names of the functional group? \n

A) I and II

B) II and IV

C) III and IV

D) II and III

B) II and IV

Consider the molecule *donepezil* (used to treat Alzheimer's disease). Which of the following lists the correct functional groups present in *donepezil*?

\
A) Amide, aromatic, ether, ketone. B) Amide, aromatic, ester, ketone. C) Amine, aromatic, ester, ketone. D) Amine, aromatic, ether, ketone.

D) Amine, aromatic, ether, ketone.

Consider the molecule *atenolol* (a β blocker used to treat hypertension). Which of the following lists the correct functional groups present in *atenolol*?

\
A) Primary alcohol, amide, primary amine, aromatic, ether.

B) Secondary alcohol, amide, secondary amine, aromatic, ether. C) Secondary alcohol, amide, primary amine, aromatic, ether.

D) Secondary alcohol, amide, secondary amine, aromatic, ester.

B) Secondary alcohol, amide, secondary amine, aromatic, ether.

Which of the following structures contains a secondary amine?

\
A) I

B) II

C) III

D) IV

C) III

Which of the following structures contains a primary amine?

\
A) I

B) II

C) III

D) IV

A) I

Which of the following structures contains an amide?

\
A) I

B) II

C) III

D) IV

D) IV

Which of the following structures contains an alkene?

\
A) I

B) II

C) III

D) IV

B) II

Which of the following is a tertiary amine?

\
A) I

B) II

C) III

D) IV

B) II

Which of the following is a secondary alcohol?

\
A) I

B) II

C) III

D) IV

D) IV

Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces?

\
A) The larger the surface area, the weaker the intermolecular force.

B) The larger the surface area, the stronger the intermolecular forces. C) The smaller the surface area, the stronger the intermolecular forces. D) There is no relationship between surface area and intermolecular forces

B) The larger the surface area, the stronger the intermolecular forces.