Introductory Organic Chemistry Final

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NAME: Banner #: PEAS 2203 – Organic Chemistry for Process Engineers – Midterm February 23, 2021 Answer all questions in the space provided. 1. ______/10 2. ______/10 3. ______/10 4. ______/8 5. ______/7 6. ______/10 7. ______/15 8. ______/15 9. ______/15 10. Bonus (1 pt) Total: ______/100 + bonus 1) Your roommate synthesized the compound below in lab last week. a) Identify all the carbonyl groups with a circle and indicate which are part of an aldehyde, ketone and carboxylic acid. (3 pts) b) What is the hybridization of the carbon indicated with the ‘A’? (1 pts) sp3 c) What is the bond geometry at the carbon indicated with the ‘B’? (1 pt) trigonal planar d) How many sp2 hybridized carbon atoms are in this structure? (1 pts) 9 e) What is the bond angle about the carbon marked with the C? (1 pt) ~109 oC f) Explain why hydroxyl group D is more acidic than hydroxyl group E. (3 pts) The conjugate base of D has the negative charge on an oxygen atom but it is stabilized by resonance. The conjugate base of E also has a negative charge on oxygen but there is no additional stabilization by resonance. Therefore, the conjugate base of D is more stable than E. Since the strongest acid gives the most stable base, group D is most acidic. 2 2) Complete the following acid-base reaction, using curved arrows to show the movement of electrons. Draw Lewis structures for all reactants and products, showing formal charges and lone pairs of electrons. Label all acids and bases and indicate whether the forward or reverse reaction is favoured. Briefly explain (with a few key words) why the equilibrium is in the direction indicated. (10 pts) base acid conjugate acid conjugate base Forward rxn favoured because a negative charge on O is more stable than a negative charge on C due to electronegativity. 3 3) Name the following compounds, being sure to indicate E and Z and cis and trans where necessary. (10 pts) a) (cis)-1-chloro-2-methylcyclohexane b) (Z)-hex-3,5-dien-2-amine ( or 3-cis) c) (E)-4-ethyl- 5-methylhex-2-enoic acid (or trans) d) (E)-2-methylhex-4-en-3-one (or trans) e) trans-3-isopropylcyclopentanol 4 4) Show the valance electrons and draw all significant resonance structures for the following molecule. (8 pts) 5) Name this compound. Of the three possible staggered Newman projections, draw the most stable, looking down the bond from carbons 1 to 2. (7 pts) 3-chlorobutan-1-amine 5 6) Which of these two substituted cyclohexanes is the most stable? Explain. (Hint: Start by drawing the chair conformations of each.) (10 pts) The trans isomer on the right can be drawn in a chair conformation so that both substituents are in equatorial positions. Steric strain is minimized when substituents are in equatorial positions. The cis isomer on the left can only be drawn with one substituent in the equatorial position. The other substituent must be in an axial position. A substituent in the axial position introduces steric strain. Therefore, the trans isomer on the right is most stable (it can minimize steric strain by having both substituents in the equatorial position). 6 7) Complete the following reactions by showing just the product/s). Mechanisms are not necessary. (15 pts) a) b) c) d) e) 7 8) Predict the product of this reaction. Draw the mechanism, showing all valence electrons. Used curved arrows to show the movement of those electrons. (15 pts) 8 9) Propose a synthesis for the following transformations. (15 pts) a) b) 9 10) Please submit your responses collated in a single document in the same order as presented here (i.e., make sure they are in order of #1, 2, 3, etc). If you do this, I’ll award a single bonus point. 10 Chapter 1: Lewis Structures, Resonance and Polarity Nomenclature Chapter 2: Acids and Bases Chapter 3: Alkanes Chapter 4: Alkenes Chapter 5: Reactions of Alkenes Chapter 6: Chirality Chapter 7: Substitution and Elimination Reactions Chapter 8: Alcohols, Ethers and Thiols Chapter 9: Benzene and Derivatives
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