Set 1 with Exams

Set 1 with Exams - Chem 210 Training Set I Organic...

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Chem 210 Training Set I Page 1 of 16 Organic Chemistry: Chem 210 Training Set I The questions are arranged approximately in the order of the coverage of material in the lecture. This set covers the material of the first exam. 1. A σ bond is made by the overlap of an sp 2 hybrid with an s orbital as shown below. What is the best graphical representation of the σ bond that forms at the same time? 2 . Here is a comparison of σ and π bonds. Which statement is false ? a) σ bonds are formed by head-to-head overlap of atomic orbitals, while π bonds are formed by lateral overlap. b) σ bonds have increased electron density on the bond axis, while π bonds have no electron density on that axis. c) σ bonds have always lower energy than π bonds. d) A rotation around σ bonds does not change the overlap, while rotation around π bonds leads to the diminished overlap. e) Only one σ bond, but one or two π bonds can exist between two atoms. 3 . Which of the following statements about sp 2 orbitals is not true ? a) they are always present as a set of three sp 2 orbitals b) they are usually used to form σ bonds (sometimes lone pairs) c) they are 33% s d) the ideal angle between two sp 2 orbitals is 120° f) e) d) c) b) a) σ bond
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Chem 210 Training Set I Page 2 of 16 4 . In a hypothetical molecule, a four-bonded carbon atom uses one sp and two sp 5 hybrids to make three of its bonds. What is the remaining hybrid that is used to make the fourth bond? a) pure s e) sp 3 b) pure p f) sp 4 c ) s p g ) s p 5 d) sp 2 h ) s p 6 5 . What are the hybridizations of the two oxygens in the acetate anion (CH 3 CO 2 )? a) both sp 3 b) both sp 2 c) both sp 2.5 d) one sp 2 and one sp 3 6. Ammonia undergoes a rapid “flip”, wherein the hydrogens move from one side of the nitrogen atom to the other (like an umbrella in the wind), as shown in the diagram below. At the lowest energy points, the lone electron pair on nitrogen resides in an sp 2.1 hybrid, but during the flip the hybridization of nitrogen changes continuously to finally reach the hybridization of the starting point again. What is the orbital that the lone pair resides in at the highest energy point during that transformation? a) s b) p c) sp d) sp 2 e) sp 3 f) sp 4 g) sp 5 h) π 7. Let’s assume that the H-P-H bond angle in PH 3 is 90 o (it really is 92 o ). What is the nature of the orbital holding the lone electron pair? a) sp 3 hybrid d) pure s b) sp 2 hybrid e) pure p c) sp hybrid f) intermediate between sp 3 and sp 2 N H H H N H H H N H H H (all atoms are in one plane) Energy
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Chem 210 Training Set I Page 3 of 16 8 . Which of the following molecules have at least one sp hybridized carbon atom? O CO CH 3 CN CO 2 OH I II III IV V VI a) I, II, IV, VI b) II, III, IV, VI c) III, V, VI d) III, IV, VI 9. Which molecules have at least one atom that is sp 2 hybridized?
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Set 1 with Exams - Chem 210 Training Set I Organic...

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