1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound?

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1 CEM 331: Chapter 1/2: Structures (Atoms, Molecules, Bonding) 1. What are the respective hybridizations of the atoms numbered 1 to 4 in this compound? N C 2 C N C 2 C N : three sigma bonds and a lone pair = sp 3 2: three sigma bonds = sp 2 3: four sigma bonds = sp 3 4: two sigma bonds = sp 2. What hybrid orbitals are used to form the sigma bond between C-1 and C-2, respectively, in the structure shown? C 3 C 3 C C C N 1 2 sp 2 and sp 3. In which of these structures would the sulfur atom be assigned a formal charge of +1? C 3 S C 3 C 3 S C 3 S C 3 S Charge = 0 Charge = +1 Charge = +2 Charge = 0 Chapter 3: Alkanes 4. There are four different functional groups in the molecule below. Identify the types of functional groups. amine 2 N amide ester N 2 ether

2 5. The heat of combustion of neopentane is kj/mol; that of pentane is kj/mol. Which statement best describes the relative stability of these two compounds? Neopentane is 2,2-dimethylpropane and is a constitutional isomer of pentane. a. Pentane and neopentane are isomers and therefore exhibit the same stability b. Pentane is more stable than neopentane by 19 kj/mol. c. Neopentane is more stable than pentane by 19 kj/mol. d. Neopentane and pentane are not isomers so no statement can be made regarding relative stability. 6. Write the IUPAC name for the following: C 3 C C 3 C 2 C 2 C 2 C 2 C 2 C 3 C C 3 C 3 2,2,8-trimethylnonane 7. Which Newman projection represents the most stable conformation of 3- methylpentane (C 3 C 2 C(C 3 )C 2 C 3 ) when viewed down the 2-3 carbon-carbon bond? C 3 C 2 C 3 C 3 C 3 C 2 C 3 C 3 C 2 C 3 C 3 C 2 C 3 C 3 C 3 smaller Gauche two Gauche larger Gauche C 3 C 3 wrong compound 8. Which compound will have three peaks of equal height and three valleys of equal depth in a diagram of potential energy vs. angle of rotation for one complete rotation around the C-C bond? C C C C C C C C The second compound will have the energy diagram where the hills and valleys are all equal in energy because the second carbon has the same three substituents (all s) and every staggered and every eclipsed conformation will be the same.

3 Chapter 4: Cycloalkanes 9. What factor is responsible for a greater heat of combustion per C 2 for cyclopropane than the heat of combustion per C 2 for cyclohexane? a. Cyclohexane has a different hydrogen-to-carbon atom ratio than cyclopropane. (the ratio is the same) b. Cyclohexane is a strained ring relative to cyclopropane (cyclohexane is the least strained ring) c. Cyclopropane is a strained ring relative to cyclohexane d. Cyclohexane has more carbon atoms than cyclopropane. (question asks per C 2, therefore not based on how many carbons there are) 10. What is the IUPAC name for this compound? a. ortho-bromocyclohexanol b. cis-2-bromocyclohexanol both are up c. endo-2-bromocyclohexanol d. trans-2-bromocylohexanol 11. Which is the most stable conformation for cis-1-bromo-3-methylcyclohexane? diequatorial and both up or both down C 3 C 3 C 3 C 3 Chapter 5: Stereochemistry 12. What is the correct stereochemical description of the relationship between this pair of compounds (identical, constitutional isomers, enantiomers, diastereomers)? Draw them in their 2-dimensional state: and rotate CW:

4 13. Which statement about these Fischer Projections is correct? C 3 C 3 C 3 C 3 C 3 C 3 a. I and II are enantiomers. no the top chiral center is the same b. II and IV are identical no both chiral centers are mirror images c. II is a meso compound no no plane of symmetry d. I and II are diastereomers yes the top chiral carbon is the same, and the bottom one is a mirror image. C 3 I II III IV C Which of these molecules are meso isomers? The middle compound has two chiral carbons and a plane of symmetry (sort of diagonally through molecule rotate that if you need to see it better) 15. Determine if each of the configurations in each of these two molecules is R or S. Assignment of priorities, then manipulate so #4 is in back for each 3 C 3 C 2 C S S C 2 2 C What is the stereochemical classification of (1S, 2S)-1,2-cyclohexanediol and (1R, 2S)-1,2-cyclohexanediol? a. enantiomers b. diastereomers c. meso compounds d. racemates If one chiral center is the opposite but the other is the same, then they are diastereomers. 4 2 R C 3 C 2 C 3 3 1

5 17. Which statement is true? a. Compounds with R stereocenters rotate plane-polarized light clockwise. [R/S have no relationship with (+)/(-)] b. For equal concentrations and equal path lengths, solutions of (+) and (-) enantiomers rotate plane-polarized light equally, but in opposite directions c. Racemic mixtures can rotate plane-polarized light either clockwise or counterclockwise. [Racemic mixtures cancel each other out rotation of 0] d. Meso compounds can rotate plane-polarized light either clockwise or counterclockwise. [Meso compounds aren t optically active rotation of 0] 18. Which of the following molecules is the enantiomer of this molecule? 3 C C 2 C 2 3 C C 3 C 2 C 2 3 C C 2 3 C 19. ow many stereocenters (chiral centers) are present in this molecule? 3 C 3 C 3 * * * C CC Which of these molecules could have an enantiomer? meso no Yes no chiral C s no chiral C s 21. Which is capable of exhibiting cis-trans isomerism? (C 3 ) 2 C C C 3 C C CC 3 C 3 C CC 3 linear no ring yes no Trisubstituted no not disubstituted

6 22. Which molecule shown below is the same stereoisomer as the one in this Fischer projection? C 3 C 3 C 3 = C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 mirror 3 C C 3 rotate into eclipsed: 3 C 3 rotate into eclipsed: 3 C 3 meso diastereomer same meso Chapter 7: Intro to Alkenes 23. What is the IUPAC name for this compound? a. (E)-3,5-dimethyl-2-hexene b. (Z)-3,5-dimethyl-2-hexene c. (Z)-1,2-dimethyl-2-isobutylethylene d. (E)-3,5,5-trimethyl-2-pentene C 3 C 3 C 2 C(C 3 ) 2 Six carbons, double bond between 2 and 3, two extra methyls on 3/5. igh priority on left is C 3 and high priority on right is larger carbon group. pposite = E. 24. What would be the stereochemical classification of the major product of this reaction? C 3 C C(C 3 ) 2 a. R-enantiomer b. S-enantiomer c. Achiral no chiral carbons d. Racemic

7 25. Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would be: a. a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial. b. a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial. c. a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial. d. A meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial. 2 down up Chapter 8: Alkene Reactions 26. What set of reagents would convert C the alkene in this alcohol 3 as the major product? a. 2, + equals C 3 C C 3 C C 2 C 3 C b. B 3 followed by Na, 2 2 c. g(ac) 2, 2 followed by NaB 4 d. followed by Na Answer (a) would work on paper but the carbocation must form next to a quaternary carbon with lots of possible methyl groups that can do methide shifts! Carbocations rearrange! Answer (b) makes the incorrect regiochemistry Answer (d) would do SN2 and E2 with Na, so two products form. C 3 C 3 C C Draw the product of the following reaction: BD 3 is just like B 3 but its easier to see the placement of the new D: 1. BD 3 2. Na, 2 2 C 3 C D 3

8 28. What intermediate is involved in the reaction shown? C 3, K C C C C dichlorocarbene 29. The addition of bromine, 2, to the alkene shown will give 2 a. one meso compound b. one pair of enantiomers c. two meso compounds d. four stereoisomers Achiral plus achiral = not optically active (and with a methy on the left and ethyl on the right, it cannot be a meso compound) Chapter 9: Alkynes and Reactions 30. What is the major product isolated from the reaction shown? Markovnikov = Methyl ketone! C 3 C 2 C C 2, gs 4 2 S 4 C 3 C 2 CC 3 C 3 C 2 C 2 C C 3 C 2 CC 2 C 3 C 2 CC What reagent(s) can be used to reduce a triple bond to a double bond having Z (cis) geometry (as shown in the figure)? R' R a. Na, N 3 b. NaB 4 c. 2, Pd/CaC 3 /Pb d. 2, Pd/C R' R Chapter 10: Radicals 32. For which free radical can the most resonance forms be written that show the delocalization of the radical? a. b. c. d. C 2 C 2 C no resonance no resonance 4 resonance forms SEVEN resonance forms!!

9 33. Which of the indicated sites would most readily undergo hydrogen atom abstraction to generate a radical? #2 1 3º allylic 2 1º C 3 3 C C º 3º 34. What is the expected stereochemistry of the organic product from this reaction? C 3 2, light C 3 + a. (S)-isomer only b. (R)-isomer only c. equal amounts of (R)-isomer and (S)-isomer can t control stereochemistry in radical reaction d. unequal amounts of (R)-isomer and (S)-isomer 35. Which radical is the most stable? C 2 C 3 C 3 C 3 C 3 1º C 3 3º C 3 2º allylic C 3 3º allylic Chapter 11: Substitutions and Eliminations 36. The reaction of benzyl bromide (C 6 5 C 2 ) with azide ion (N 3 ) is C 6 5 C 2 + N 3 C 6 5 C 2 N 3 + shown in the box. When the benzyl bromide concentration is constant and the azide concentration doubles, the reaction rate is observed to increase by a factor of two. When the azide concentration is held constant and the benzyl bromide concentration doubled, the rate of the reaction doubles. What is the correct rate law for this reaction? a. Rate = k [C 6 5 C 2 ] 2 [N 3 ] 2 b. Rate = k [C 6 5 C 2 ] 4 [N 3 ] 2 c. Rate = k [C 6 5 C 2 ] 2 [N 3 ] d. Rate = k [C 6 5 C 2 ] [N 3 ] SN2 reaction Rate = k[nuc][rx]

10 37. What is the structure of the reagent that would yield the two products shown?? C 3 C 3 C 6 C SN1 and E1 reaction with neak nucleophile/base need alkyl halide where SN1 occurs: C 6 5 C 6 5 C 6 5 C What is the expected reaction pathway (E2, E1, S N 2, S N 1) for the following reaction? C 2 C 2 C 3 C 2 C C 1º alkyl halide with strong nucleophile = SN2 39. What is the configuration of the substitution product formed from the reaction of K with (R)-1-chloro-1-deuteriobutane (C 3 C 2 C 2 CD)? a. (S)-1-deuterio-1-butanol b. (R)-1-deuterio-1-butanol c. meso-1-deuterio-1-butanol3 d. a racemic mixture of (a) and (b) D R 1º K SN2 D S 40. Put the nucleophiles (C 3, C 3, C 3 N 2 ) in order, fastest to slowest, for reaction with propyl bromide (C 3 C 2 C 2 + Nuc C 3 C 2 C 2 Nuc). Strongest nucleophile has anion (C 3 ). The other two nucleophiles are neutral. Which is a stronger nucleophile oxygen or nitrogen? Which one is more willing to give up its electrons? Nitrogen. Why? Its less electronegative so more willing to share its electrons. rder? C 3 C 3, C 3 N 2, C Which alkyl halide would you expect to undergo S N 1 hydrolysis most rapidly? a. (C 3 ) 3 CI b. (C 3 ) 3 C c. (C 3 ) 3 C d. (C 3 ) 3 CF best leaving group is iodide

11 42. Which anion is the most nucleophilic towards methyl iodide in an S N 2 reaction? C 3 C 2 C 2 S C 3 C 2 C 2 C 3 C 2 C 43. What is the major elimination product from the reaction shown? D C 3 KtBu Need to ring flip first: D D C 3 E2 with trans-diaxial hydrogen/halide C3 44. What is the product of the reaction shown? 3 C D C 6 5 KtBu Rotate left chiral carbon to put in antiperiplanar position: D C 3 3 C Ph C 6 5 = Ph (phenyl) Ph D 45. What would be the possible product(s) of the dehydrohalogenation of trans-1- bromo-2-methylcyclohexane? K C 3 C 3 C 3 C 3

12 46. Why would concentrated hydrobromic acid be an inappropriate catalyst for the dehydration of alcohols? a. is too weakly acidic to protonate the alcohol. Not true! Used to convert 3º alcohols to 3º bromides b. The conjugate base,, is a good nucleophile and it would attack the carbocation to form an alkyl bromide. c. is strongly acidic, so the water molecule would not be a good leaving group after protonation of the alcohol. False! d. would be more like to promote rearrangement of the carbocation intermediate. No more than any other acid involved in a reaction that makes a carbocation. 47. Which carbocation is not likely to undergo rearrangement? Already most stable: 48. Which alcohol is dehydrated fastest in concentrated 2 S 4? 3º alcohols do E1 fastest C 3 C 2 CC 3 C 3 C 2 CC 2 C 3 CCC 3 C 3 CC 2 C 2 C 3 C 3 C 3 C Consider the following typical nucleophilic substitution reaction. The effect of doubling the C 3 + K C 3 + K volume of solvent would be to multiply the reaction rate by a factor of: a. ¼ b. ½ c. 2 d. 4 Tricky question if you double the solvent volume, you cut the concentration of both the nucleophile and the alkyl halide in half. If you cut them BT in half, you cut the rate to a quarter of its original rate.

13 Chapter 18: Ethers 50. Which set of products is expected from the reaction shown? C 2 C 3 heat a. b. c. d No Reaction C 2 C 3 C 2 C 3 C 2 C What is the product of the reaction shown? C 3 NaC 3 3 C C Which reaction would product phenyl propyl ether? a. b. Na C 3 C 2 C 2 Na C 3 C 2 C 2 c. d. C 3 C 2 C 2 Na C 3 C 2 C 2 Answer (b) has no leaving group, (c) cannot do SN2 on sp 2 nucleophile. carbon and (d) has no 53. Which of the following molecules shown below is the product of the reaction of (E)-1-phenylpropene with meta-chloroperbenzoic acid? C 3 mcpba Epoxide maintain stereochemistry! C 3 C 2 C 3 C 3

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