Chemistry 310N Dr. Brent Iverson Final May 11, 2006 NAME (Print): _____________________________ SIGNATURE: _____________________________ Please Note: This test may be a bit long, but there is a reason. I would like to give you a lot of little questions, so you can find ones you can answer and show me what you know, rather than just a few questions that may be testing the one thing you forgot. I recommend you look the exam over and answer the questions you are sure of first , then go back and try to figure out the rest. Also make sure to look at the point totals on the questions as a guide to help budget your time. Note: You must have your answers written in pen if you want a regrade!!!! Please print the first three letters of your last name in the three boxes For synthesis problems GO FOR PARTIAL CREDIT EVEN IF YOU DO NOT KNOW THE ENTIRE ANSWER!!!WRITE DOWN WHAT YOU DO KNOW IS IN THE REACTION SEQUENCE SOMEWHERE. YOU WILL GET PARTIAL CREDIT IF IT IS CORRECT
10 9 8 7 6 5 4 16 15 (30) (33) (20) (32) (21) (30) (20) (19) (35) (35) (21) (22) (17) (10) (23) (21) (389) 11 14 Total T Score 12 13 3 2 1 Page Points
CH 3 CH 2 - H R 2 C C H H H -N( i- C 3 H 7 ) 2 RC C H COR' O RC H 2 CR' O RC H 2 CH O RC H 2 CCl O RC H 2 RCH 2 O H HO H ROC O COR' O C H 2 RC O COR' O C H 2 RC O CR' O C H 2 H 4 N CO- H O R RCH 2 O H 2 H 3 O H -Cl 10 51 -7 Compound pK a 3-5 15.7 16 18-20 11 23-25 18-20 13 15-19 40 Carboxylic acids β -Dicarbonyls β -Ketoesters β -Diesters Water Alcohols Acid chlorides Aldehydes Ketones Esters LDA Alkanes Terminal alkynes 25 Terminal alkenes 44 9.2 Ammonium ion Hydronium ion Hydrochloric acid Protonated alcohol -2 -1.7
Signature_________________________ Pg 1 _____________(30) True False 2. (2 pt. each) Here are a number of statements regarding general aspects of organic chemistry. Do not second guess yourself, this is not meant to be tricky! Check the appropriate box to indicate whether the statement is true or false. B. Resonance contributing structures generally are used to describe pi electron delocalization. A. Resonance contributing structures generally involve moving lone pairs and pi bonds between atoms. C. The exceptions to the VSEPR model we saw this semester involved pi electron delocalization. D. In 1 H-NMR, signals for H atoms attached to more electronegative atoms appear closer to TMS than the signals for H atoms attached to less electronegative atoms. E. A carbocation can be stabilized by either hyperconjugation or resonance. F. In 1 H-NMR, spin-spin splitting is caused by induced electron density movement that in turn induces small magnetic fields. G. Enolates are great electrophiles 1. (14 points) Suppose a relative of yours is having an MRI. In no more than four sentences, explain to them what is happening when they have the MRI scan. We will be looking for a minumum of 7 key points here. H. When a reaction is under kinetic control, the more stable product is the predominant one (greater motive), while when a reaction is under thermodynamic control the product that forms faster (better opportunity) is the predominant one.
Signature_________________________ Pg 2 _____________(33) 3. (8 points) For the following molecules, write the correct hybridization state of the atoms indicated by the arrows.
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