CHEM 207 (A) 1. Midterm Exam 11.11.2010 Name: Student Number: Signature: 1) The __________ tells us that each orbital can hold a maximum of 2 electrons. A) Pauli exclusion principle B) uncertainty principle C) aufbau principle D) Hund's rule principle E) LeChatelier principle 2) Provide a Lewis structure for a molecule with molecular formula CH2O2. 1) _______ 2) _____________ 3) Write a Lewis structure for a compound with the molecular formula H2N2. 4) The compound methylamine, CH3NH2, contains a CN bond. In this bond, which of the 4) _______ following best describes the charge on the carbon atom? A) +1 B) slightly positive C) uncharged D) slightly negative E) -1 1 5) The electronegativity of elements on the periodic table increases going __________ a column and to the __________ in each row. A) up, left B) down, left C) down, right D) up, right 5) _______ 6) Which of the following are correct Lewis structures, including formal charges, for nitric acid, HNO3? 6) _______ A) B) C) D) E) A only B only C only both B and C A, B, and C 7) One resonance structure of a cation is shown. Provide the other reasonable resonance structures. 7) _____________ 8) Provide the structural Formula (showing all bonds) for an aldehyde whose condensed structure is (CH3)3CCHO. 8) _____________ 9) Provide the line-angle formula for the alcohol CH3CH2CH(OH)CH2CH2CH(CH3)2. 9) _____________ 2 10) Provide the products of the following acid-base reaction. 10) _____________ (CH3)3NH+ + HO-→ 11) When methanol (CH3OH) acts as a base, its conjugate acid is __________. A) -CH2OH 11) ______ B) CH4O+ C) CH3OH2+ D) CH3OE) CH4OH 12) Which of the following pairs of bases lists the stronger base first? A) H2O > HOB) CH3COO- > HO- 12) ______ C) HO- > H2ND) I- > ClE) H2N- > CH3COO13) Consider the species CH3O-, NH2-, and CH3COO-. Rank these ions in order of increasing basicity, and explain your rationale. 14) Complete the following chemical reaction and predict whether the equilibrium will favor the reactants of products . Briefly explain why: 14) _____________ 3 15) Which atomic orbital combination would result in a molecular sigma bond? A) B) C) 15) ______ D) 16) Consider the interaction of two hydrogen 1s atomic orbitals of the same phase. Which of the statements below is an incorrect description of this interaction? A) The molecular orbital formed is cylindrically symmetric. B) A sigma bonding molecular orbital is formed. C) The molecular orbital formed has a node between the atoms. D) A maximum of two electrons may occupy the molecular orbital formed. E) The molecular orbital formed is lower in energy than a hydrogen 1s atomic orbital. 16) ______ 17) Based on the structure below, what is the value for the H-N-CH3 bond angle? Briefly explain 17) ______ why. A) 109 degrees B) 90 degrees C) 60 degrees D) 120 degrees 18) In the structure below, the sigma bond of the carbonyl is formed from the overlap of a(n) __________ orbital of carbon and a(n) __________ orbital of oxygen. A) sp2, sp2 B) sp, sp2 19) Show the bonding scheme for the molecule below. C) p, p 18) ______ D) sp3, sp2 19) ______ 4 20) What intermolecular forces are present among molecules in dimethyl ether, CH3OCH3? A) B) C) D) 20) ______ both London dispersion forces and dipole-dipole forces London forces only both London dispersion forces and hydrogen bonding hydrogen bonding only 21) Which of the molecules below has the higher boiling point? Briefly explain your choice. CH3CH2CH2OH or CH3CH2OCH3 22) Which of the molecules below has the higher boiling point? Briefly explain your choice. CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3 5 1) A 2) 3) 4) B 5) D 6) B 7) 8) 9) 10) (CH3)3N + H2O 11) C 12) E 6 13) CH3COO- < CH3O- < NH2The first factor to consider is the nature of the atom which bears the negative charge. The more electronegative the atom that bears the negative charge, the more stable the anion. Stable anions are less reactive and are hence weaker bases. Since O is more electronegative than N, the NH2- is the strongest base in the set. In the remaining two species, the negative charge is on the O, but in the case of CH3COO-, the negative charge is also delocalized by resonance. 14) 15) 16) 17) 18) 19) 20) 21) The stronger acid and the stronger base are both on the left side of the reaction (reactants); therefore, the equilibrium concentration should favor the products or right side of this equation. B C D A B A CH3CH2CH2OH has the higher boiling point since it is capable of intermolecular hydrogen bonding. 22) CH3CH2CH2CH2CH3 has the higher boiling point. As the degree of branching increases, the surface area of the molecule decreases and the potential for intermolecular attraction via London forces decreases. Greater surface area leads to a more intermolecular attraction which in results in a higher boiling point. 7