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CHEM 2411 – Organic Chemistry I Chapter 2: Additional Problems 1) Rank the following compounds in order of increasing acidity (i.e., x < y < z) a b Cl O Cl O O F H c Br O H Br d O Cl O H O F O H F c<b<d<a 2) A 250.0 mM aqueous solution of an acid HA has a pH of 5.2. What is the pKa of HA? If pH = 5.2, and pH = -log [H3O+], then [H3O+] = 10-5.2 = 6.3 × 10-6, and [A-] = 6.3 × 10-6 Now determine Ka based on the equation Then pKa = -log Ka = 9.8 3) Provide the skeletal structures for the following: a) (CH3CH2)3N N b) CH3CH(OH)CH(OH)CH(OH)CH3 OH OH OH 4) What kind on molecular orbital (σ, σ*, π, or π*) results when the two atomic orbitals shown below interact in the manner indicated? Answer: π 5) The atomic number of boron is 5. The correct electronic configuration of boron is: A) 1s22s3 B) 1s22p3 C) 1s22s22p1 D) 2s22p3 E) 1s22s23s1 Answer: C 6) Draw a correct Lewis structure for boric acid, B(OH)3. Answer: or 7) In the structure below, the sigma bond of the carbonyl is formed from the overlap of a(n) ________ atomic orbital of carbon and a(n) ________ atomic orbital of oxygen. A) sp, sp2 B) sp3, sp2 C) sp2, sp2 D) p, p Answer: C 8) Complete the structure of methyl azide by adding any necessary formal charges. Answer: 9) Which of the following condensed formulas represents the same compound as the line-angle structure shown? A) CH3CH2CH2OCH2CH2CH2N(CH2CH2CH3)2 B) CH3CH2CH2OCH2N(CH2CH3)2 C) CH3CH2OCH2N(CH2CH3)2 D) CH3CH2OCH2N(CH2CH2CH3)2 E) CH3ON(CH3)2 Answer: C 10) Calculate the empirical and molecular formulas of the compound with molecular weight 122 and an elemental analysis of 59.01% C, 4.97% H, 13.12% O, and 22.90% N. Answer: Empirical and molecular formulas are the same: C6H6N2O.