A 1 Chemistry 230 ♦ Fall 2009 ♦ Dr. Glazer Chemistry 230 (Fall 2009) Midterm Exam 1 75 minutes, 100 points Your Name (Please Print) : ________________KEY____________________________________ Your ID # : ___________________________________________________________ Tear off the ANSWER PAGE at the back of the exam. FILL IN YOUR NAME AND ID#. Please mark your answers clearly ON THE ANSWER PAGE. It is this page ONLY that will be graded! Make sure you read the questions carefully and answer all parts. A periodic table is attached at the back of the exam, along with a page of scratch paper. No electronic devices are allowed. Have your ID visible on the table. GOOD LUCK!A 2 NAME (please print):_______________________________ First Last 1) (8 points) Draw Lewis structures for each of the following molecules (include lone pairs and formal charges). Draw resonance structures where appropriate. Label the major and minor contributors: A) CO B) HCONH2 2) (8 points) Draw all the isomers with the formula C4H8.A 3 NAME (please print):_______________________________ First Last 3) (10 points). Indicate whether equilibrium lies to the LEFT or to the RIGHT for the following reactions. NH2 + CH3SHHCN + CH3CH2OCN + CH3CH2OHNH3 + CH3SCH3CH2OH + CH3SCH3CH2O + CH3SHA)B)C) D) The pKa of CH3CH2OH = ____. E) The pKa of NH3 = _____. 4) (12 points) The marked hydrogen is very acidic. Why? (Hint: you will have to draw all relevant structures to support your explanation.)A 4 NAME (please print):_______________________________ First Last 5) (15 points) Consider the following two molecules. Draw all resonance structures (no more than 5) for the CONJUGATE BASE OF THE MORE ACIDIC molecule. 6) (10 points) DMAP (4-dimethylaminopyrdine) is an important molecule used in many reactions. The different N atoms have been labeled as “N1” and “N2”. For your answer, write “N1” or “N2”. A) Which N is more basic? B) Which N is more nucleophilic? NNDMAP =N1N2OHOHNO2NO2A) B)A 5 NAME (please print):_______________________________ First Last 7) (12 points) Name the following functional groups. Identify the hybridization of the indicated carbons. OOHH NA) B) C) D)O 8) (8 points) The important antioxidant molecule glutathione is shown below. Name the functional groups indicated by the arrows (and circle). HO NHHNONH2OSHOOHOABC (Functional groupwithin the circle)DA 6 9) (9 points) The following molecule is nicotine, an important pharmacophore in tobacco. NN a) Redraw nicotine, and label the hybridization of each N atom. b) Label the geometry of each N atom. c) Label the identity of the type of orbital that the lone pair resides in for each N atom. 10) (8 points) For each of the following molecules, provide the following information: Is the molecule polar or nonpolar? What are the PRIMARY intermolecular forces present in each compound? nA) B)H NOC)NHNNH2OD)N2A 7A 8 SCRATCH PAPER:A 9 Chemistry 230 ♦ Fall 2009 ♦ Dr. Glazer MIDTERM 1 ANSWER PAGE NAME:________KEY_________________ ID#:_____________________________ 1) A) B) 2) 3) (Please circle the appropriate answer for A, B, and C.) A) Left Right D) pKa = 16 B) Left Right E) pKa = 35-38 C) Left Right 4) C OC OminormajorHONH NOHHHHmajorminorOOHOOOOOOHBO OpKa = 9. 2 carbonyl groups make this position very acidicas the resulting enolate ion delocalizes it charge over two carbonyl groups (3 resonance forms)A 10 5) 6) N1 or N2? A) N2 B) N2 7) A) Ester, sp2 B) Alkyne, sp C)Ketone/Enolate, sp2 D)Nitrile, sp3 8) A) Amine B) Thiol C) Amide D)Carboxylic acid 9) 10) A)nonpolar, van der Waals B) nonpolar, van der Waals C)polar, dipole-dipole D) polar, H-bond ONOONOOONOOONOOONOOONNsp3, tetrahedral, sp3sp2, triginal planar,
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