Homework - Review of Chem 2310

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Gabriel Bruce
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1 omework - Review of Chem 2310 ame 1. Fill in the following partial Periodic Table of Table of Elements. Do as much as you can from memory. 2. Using the Table above, circle the more electronegative atom in each pair. nitrogen oxygen carbon hydrogen chlorine carbon carbon nitrogen e) oxygen fluorine f) carbon oxygen 3. What is an isotope? 4. Give the number of valence electrons of each of the following elements. oxygen hydrogen chlorine lithium e) bromine f) nitrogen g) iodine h) carbon i) sodium j) aluminum k) boron l) sulfur m) magnesium n) phosphorus o) potassium 5. Draw the Lewis structure for each of the following elements, and tell how many covelent bonds you would expect each to form (no charges). carbon oxygen e) bromine g) sulfur nitrogen hydrogen f) phosphorus h) chlorine

2 W Review p 2 6. Draw complete Lewis structures for three compounds with the formula C 2 5 (and no charged atoms). 7. Give the molecular formula for the following line structures Give the unsaturation number for each of the following molecular formulas, and draw one possible structure for each. C 5 10 C 5 12 C 5 11 C Give the geometry of all atoms (except hydrogen) in each of the following compounds.

3 W Review p Label the polar bonds in each of the following molecules (ignore C- bonds) using partial charges (!+,!-) or polarity arrows. 11. Give the hybridization of each atom (except hydrogen) in the following compounds. 12. Label each molecular orbital and give the atomic orbitals that it came from in the following compound. d e f) a b c i f g h e) 13. Draw resonance structures for the following compounds, using arrows to show where the electrons go. g) h) i)

4 W Review p Give the charge next to each atom in the following compounds which has a charge. e) f) 15. Give all functional groups which the following compounds contain. 2 e) f) 16. What functional groups do the following compounds contain? 2-pentyne 2-pentanone trans-2-pentene methyl pentanoate e) pentanal f) 2-cyanopentanoic acid g) 2-pentanol h) 2-pentanamine

5 17. Which intermolecular force will be the most important in the the following compounds? W Review p 5 e) f) 18. Choose the compound in each pair which will have the highest boiling point, and briefly explain your choice. e) Choose the compound in each pair which will be the most soluble in water, and briefly explain your choice. 2

6 W Review p Assign each of the following IR's with one of the compounds shown (not all compounds will be use. A C B D E F G 2

7 W Review p Give the relationship between each of the following compounds (identical, constitutional isomers, enantiomers, diastereomers, meso, not isomers). 2 2 e) f) g) h) 22. Draw correct line structures for the following compounds. 3-ethylhexane 1-chloro-1-methylcyclopropane (Z)-3-methyl-2-pentene (R)-2-bromopentane e) 3-methyl-4-penten-1-yne f) bicyclo[0.3.4]nonane g) 2-cyclopropylbutane h) cyclononyne i) (trans)-1,3-hexadiene

8 W Review p Give correct names for the following structures. e) f) 24. Circle the stronger acid in each pair, and briefly explain your choice. S e) Draw the Fischer projection for the following compound.

9 W Review p Draw a chart showing the chemical shift, integration, and splitting for each of the following spectra. Then deduce their structures. C C Choose the correct answer. If the K eq is >1, the reaction is (favorable / unfavorable). If the!g is > 0, the reaction is (favorable / unfavorable). If you take away a product from a reaction at equilibrium, more (products / reagents) will be formed. If you heat a reaction, the rate will (increase / decrease). e) If you increase the concentration of a reagent which is in the rate limiting step, the reaction rate will (increase / decrease).

10 W Review p Write the pka of the acid on each side of the equation below it; then, use them to predict whether the products or reactants will be favored by the equilibrium. + 2 S 4 + S a a ac 3 a C What is an electrophile? 30. What is a nucleophile? 31. What is the difference between a base and a nucleophile? 32. Label the following as nucleophiles or electrophiles. C 3 C e) f) 3 a + 2 g) h) C + 3 i) C 3 -

11 W Review p Using your knowledge of nucleophiles and electrophiles, draw arrows to show how the following species will react with each other (1st step only) and give the immediate product. (cold, dark) 34. Draw the complete mechanisms of the following reactions. methane + bromine + heat or light methyl bromide + + byproducts ethyl bromide + sodium hydroxide ethyl alcohol + sodium bromide tert-butyl iodide + sodium ethoxide 2-methyl-1-propene + ethanol + sodium iodide

12 W Review p 12 cyclopentene + sulfuric acid + water cyclopentyl alcohol 35. Give all products of the following reactions (except stereoisomers of chiral compounds). a 2 2 eq e) a f) g) KMn 4 2, a h)

13 W Review p 13 i) ai acetone j) a, 3 k) 2 S 4, g(a 2 2 l) 1. B 3 -TF , a m) S S a n) C 3 C 3 o) 2 p) heat q) 1. g(a 2, 2 2. ab 4 r) 2, Pd/C s) 3 2

14 W Review p 14 t) (C 3 ) 2 S u) (C 3 ) 3 CK v) KMn 4 2, a w) 3, 2 x) 2, Pt/C y) 1. disiamylborane , a z) I 2, 2 a ac b 2 eq a c Ph d 2 eq 2

15 ee) 2, Lindlar W Review p 15 ff) 2 eq a Write a reaction sequence (starting materials, reagents, and products for each step) by which the following transformations could be accomplished. (2 steps) (2 steps) (3 steps) (3 steps)

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