Organic chem 1 test 1

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Feb 20, 2024

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Organic Chemistry I Exam I 02/09/2023 - 02/10/2023
1) A nitrogen with two bonds has _______ lone pair(s) and would carry a formal charge of _______? A. 0, 1+ B. 1, 1- C. 2, 1- D. 1, 0 E. 2, 1+ 2) In the following molecule, what type of orbital is the lone pair in? A. unhybridized s B. unhybridized p C. sp³ hybridized D. sp² hybridized E. sp hybridized 3) Which of the following terms describes why primary alcohols are more acidic than secondary and tertiary alcohols? A. Induction B. Resonance C. Lewis acid-base complex D. Solvating effect E. Leveling effect 4) Which of the following compounds is the most basic? 5) Constructive interference of waves results in _________. A. A covalent bond B. A wave with larger amplitude C. Cancelation of both waves D. Formation of a node E. Both A and B 6) Which of the following is the correct condensed structure for the following compound? A. CH C(CH ) (CH ) (CH)BrC(CH ) B. CH CH CH C(CH ) C(CH ) CHBr C. (CH ) C(CH ) BrCHCH CH D. CH CH CH C(CH ) CHBrCHCH CH E. (CH ) C(CH ) CHBrCH(CH )
7) Distillation is a technique used in the purification of volatile liquids by taking advantage of their differences in boiling point. If a mixture of water, isopentane, acetone, sec-butanol, and isopropanol was found, what is the order in which the compounds would be purified (low boiling chemicals distill first)? Provide your answer by placing a number (1-5) in each box under the appropriate structure. 8) A recent publication on strategies against melanoma contained the following molecule (4-S-CAP). a) Clearly label the structure with each functional group found in the molecule. b) Which functional group contains the most acidic proton? c) An intermolecular proton transfer can take place with this compound. Draw the product formed from this proton transfer and add mechanism arrows to the structure on the left to justify your product (Next page). 9) In 1935, Louis Hammet noticed a relationship between the substituent in the para position of benzoic acid and the acidity of the carboxylic acid. Using your knowledge of factors that influence acidity, rank the following benzoic acids from 1-5 (1 = most acidic. 5 = least acidic)
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10) 4-aminobenzoic acid (PABA) was one of the first ingredients used in the initial formulation of sunscreen. Draw a mechanism (add curved arrows) converting resonance structure A into resonance structure B (Note: lone pairs are not shown for resonance structure B). 11) Draw the intermediate observed in the following Lewis acid-catalyzed reaction. 12) Which nitrogen contains a delocalized lone pair of electrons (circle)? 13) Add curved arrows to the following molecules to convert them to their conjugate bases. Next to the anion of the conjugate base, draw the expected counterion.
14) Basic red 1 is a tetracyclic compound (it has four rings) that is used as commercial dye. This compound has many significant resonance structures and the positive charge is highly delocalized. While resonance structures can be drawn in which the positive charge is spread throughout all four rings, nonetheless, one of the rings likely bears very little of the charge relative to the other rings. For simplicity, the positive charge has been shown in the center of the molecule. a) Circle the aromatic ring that is not participating as effectively in resonance and briefly suggest an explanation. b) Draw three additional resonance structures and order them from most significant to least signification. Only 1 of your structures may have a formal charge on a carbon. Most-----------------------------------------------------Least
15) In the large boxes, below draw 4 constitutional isomers with the molecular formula C H O and place a number in the smaller box ranking them from lowest boiling (1) to highest boiling (4). There are 2 conditions you must follow. 1) Each of the 4 must contain a different functional group, and 2) none of the compounds may contain an alkene.
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