a. Draw clear structures of all the possible distinct 2,3-dibromobutane isomers that can be formed. b. identifying the absolute stereochemistry of each stereocenters. c. Indicate the relationships between each of the structures you have drawn (enantiomers, diastereomers, etc.).
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- 6. The Newman projection and an equivalent 3D projection for an alkyl bromide is shown below. Under E2 conditions, there is only one major alkene product. Ph H3C H H3C. H H Br CH₂CH3 = Ph. H Br E2 conditions major product a. In 1-2 sentences, explain why only one constitutional isomer (regioisomer) forms. b. Explain why only one stereoisomer is possible for this E2 reaction. In your explanation, draw the conformation of the alkyl bromide that reacts to form product.11. Draw the compounds are in staggered conformer with the alkyl groups anti to each other. The Newman Projections must be drawn about the carbon-carbon bonds containing both stereocenters. The stereochemistry is important. CI CH3 OH H. H3C CI H HO, H3C ci CH2CH36. a. Draw both chair conformations for trans-1,2-dichlorocyclohexane. Label all unfavorable interactions. b. In 1,2-disubstituted cyclohexanes, the substituents interact not just with the ring itself, but also with each other. Draw Newman projections to explain where that interaction occurs in the chairs from part a.
- a. Draw clear structures of all the possible distinct 2,3-dibromobutane isomers that can be formed. d. Choose the (2R,3R)-dibromobutane and draw the most stable and the least stable Newman projection looking at C2-C3 sigma bond.3. Chair conformation time! Consider the following molecule: Ph. iPr NH₂ a. Circle the largest substituent. b. Now take this largest substituent and place it equatorial on one of the cyclohexane rings drawn below. It does not matter which ring you pick first. c. Now move clockwise (or counterclockwise if you're rebellious) around the chair conformation you chose, drawing in the rest of the substituents (including hydrogens). i. Remember, wedges and dashes only indicate up or down here, not axial or equatorial. You can be axial up, equatorial up, axial down, or equatorial down. d. Now look at the chair conformation you left blank. Draw the largest substituent axial on this ring. e. Repeat c, moving along the rest of the chair conformation to draw in the rest of the substituents, including hydrogens. f. Label the most stable conformation: it should be the conformation with the most and/or largest substituents equatorial. #45. Chairs and E2 b. a. Draw the line-bond structure of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Draw both chair flips of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Showing all calculations, determine which is the more stable conformation. C. Which chair flip is able to undergo E2 elimination? Justify your answer. d. Show the product of such an E2 elimination using NaOEt as base.
- 1. Draw all possible stereoisomers of the structures below. Indicate the isomeric relationships between all pairs of stereoisomers in each box. In each original structure, circle the stereocenters. D. E. NH2 OMeLocate the stereogenic centers in each molecule. Compounds may have zero, one, or more stereogenic centers. a. CH;CH,CH(C)CH,CH3 b. CH,CH(OH)CH=CH2 c. CH,CH,CH,OH d. (CHaCHCH;CH,CH(CH,)CH,CHa e. (CHa)2CHCH,CH(NH2)COOH f.5. Give the stereochemical relationship between each pair of isomers. Examples are same compound (meso), constitutional isomers, enantiomers, and diastereomers. H3C CH3 HO OH lll a. Но OH H Br CH3 b. C/ H3C CI H. ICH3 CH3 с. CH3 H. CH3 d. Но. H3C OH CH2OH Ho CH2OH Br e. Br H3C f. H CH3 H3C CH3
- - Common molecular moieties have easily distinguishable patterns in NMR spectra. Match the Tollowing hydrocarbons with the generalized spectra shown below. Label each splitting pattem as a singlet, doublet, triplet, or quartet. a. X,CH-CHY, b. X,CH-CH,Y с. ХCH-CH,Y d. XCH,CH, 4.0 3.5 3.0 2.5 2.0 1.5 2.0 1.5 1.0 0.5 0.0 5.5 5.0 4.5 4.0 6.0 5.5 5.0 4.5 4.0 Peak b2. The following molecule is one enantiomer of methylenedioxymethamphetamine (MDMA). 2a. Circle all of the stereocenters in MDMA 2b. Assign the absolute stereochemistry (R or S) for each stereocenter .CH3 HN H H *CH3Which choice correctly assigns the E/Z configuration of each alkene (I-III) shown below? H3C H3CH2C CI H2N H- HO. NCH2C NHCH3 (H3C)2HC H3CO Br H3CO I II II choose your answer... V ; I| = choose your answer... V : III = choose your answer...