Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 5.SE, Problem 68AP
Allenes are compounds with adjacent carbon-carbon double bonds. Many allenes are chiral, even though they don’t contain chirality centers. Mycomycin, for example, a naturally occurring antibiotic isolated from the bacterium Nocardia acidophilus, is chiral and has [α]D = -130. Explain why mycomycin is chiral.
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Chapter 5 Solutions
Organic Chemistry
Ch. 5.2 - Prob. 1PCh. 5.2 - Prob. 2PCh. 5.2 - Prob. 3PCh. 5.2 - Prob. 4PCh. 5.3 - Is cocaine (Worked Example 5-2) dextrorotatory or...Ch. 5.3 - Prob. 6PCh. 5.5 - Prob. 7PCh. 5.5 - Prob. 8PCh. 5.5 - Prob. 9PCh. 5.5 - Assign R or S configuration to the chirality...
Ch. 5.5 - Draw a tetrahedral representation of...Ch. 5.5 - Prob. 12PCh. 5.6 - One of the following molecules (a)–(d) is...Ch. 5.6 - Prob. 14PCh. 5.6 - Assign R or S configuration to each chirality...Ch. 5.7 - Prob. 16PCh. 5.7 - Which of the following have a meso form? (Recall...Ch. 5.7 - Does the following structure represent a meso...Ch. 5.8 - Prob. 19PCh. 5.8 - Prob. 20PCh. 5.9 - Prob. 21PCh. 5.11 - Prob. 22PCh. 5.11 - Prob. 23PCh. 5.11 - The lactic acid that builds up in tired muscles is...Ch. 5.11 - The aconitase-catalyzed addition of water to...Ch. 5.SE - Which of the following structures are identical?...Ch. 5.SE - Prob. 27VCCh. 5.SE - Prob. 28VCCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 30VCCh. 5.SE - Prob. 31APCh. 5.SE - Which of the following compounds are chiral? Draw...Ch. 5.SE - Prob. 33APCh. 5.SE - Eight alcohols have the formula C5H12O. Draw them....Ch. 5.SE - Draw compounds that fit the following...Ch. 5.SE - Prob. 36APCh. 5.SE - Prob. 37APCh. 5.SE - Prob. 38APCh. 5.SE - What is the stereochemical configuration of the...Ch. 5.SE - Prob. 40APCh. 5.SE - Prob. 41APCh. 5.SE - Prob. 42APCh. 5.SE - Prob. 43APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 46APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configurations to the chirality...Ch. 5.SE - Assign R or S stereochemistry to the chirality...Ch. 5.SE - Prob. 50APCh. 5.SE - Draw examples of the following: (a) A meso...Ch. 5.SE - Prob. 52APCh. 5.SE - Prob. 53APCh. 5.SE - Prob. 54APCh. 5.SE - On reaction with hydrogen gas by a platinum...Ch. 5.SE - Prob. 56APCh. 5.SE - Prob. 57APCh. 5.SE - One of the steps in fat metabolism is the...Ch. 5.SE - The dehydration of citrate to yield cis-aconitate,...Ch. 5.SE - The first step in the metabolism of glycerol,...Ch. 5.SE - One of the steps in fatty-acid biosynthesis is the...Ch. 5.SE - Prob. 62APCh. 5.SE - Draw tetrahedral representations of the two...Ch. 5.SE - The naturally occurring form of the amino acid...Ch. 5.SE - Prob. 65APCh. 5.SE - Prob. 66APCh. 5.SE - Prob. 67APCh. 5.SE - Allenes are compounds with adjacent carbon-carbon...Ch. 5.SE - Prob. 69APCh. 5.SE - Prob. 70APCh. 5.SE - How many stereoisomers of...Ch. 5.SE - Draw both cis- and trans-1,4-dimethylcyclohexane...Ch. 5.SE - Draw both cis- and trans-1,3-dimethylcyclohexane...Ch. 5.SE - cis-1,2-Dimethylcyclohexane is optically inactive...Ch. 5.SE - Prob. 75APCh. 5.SE - Prob. 76APCh. 5.SE - Prob. 77AP
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- NH2 NH2 of the most important properties of chiral ules in solution is their effect on plane- zed light, this effect is called optical activity. -H 2 COOH HOOC 3 H3C CH3 an enantiomer rotates a plane-polarized light e positive direction or clockwise, it is rotary (+ or d), while for a negative direction unterclockwise, it is levorotary (- or l) (+)-Alanine (-)-Alanine Alanine is a chiral amino acid that has two enantiomers: (+)-alanine and (-)-alanine. These two are optical isomers. 78. Which enantiomer of alanine rotates the plane polarized light clockwise?arrow_forwardDraw all possible constitutional isomers and stereoisomers for acompound of molecular formula C6H12 having a cyclobutane ring andtwo methyl groups as substituents. Label each compound as chiral orachiral.arrow_forwardOH OH OH 1. Hg(OAc)2, H₂O 2. NaBH4, NaOH x HỌ OH + enantiomer + enantiomer + enantiomer + enantiomerarrow_forward
- A limited number of chiral compounds having no stereogenic centers exist. For example, although A is achiral, constitutional isomer B is chiral. Make models and explain this observation. Compounds containing two double bonds that share a single carbon atom are called allenes. Locate the allene in the antibiotic mycomycin and decide whether mycomycin is chiral or achiral.arrow_forwardClassify the following compounds as chiral, achiral (but not meso), or meso. OH 1st structure: H_H OH CO₂H chiral く CO₂H HO₂C 2nd structure: 3rd structure: achiral CO₂H CO₂H CO₂Harrow_forwardClassify the following pair of compounds as the same compound, enantiomers, diastereomers, constitutional isomers, or not isomeric. Also, select the correct IUPAC name, including the correct (R) or (S) designation, for each. H ÷ ||I The correct IUPAC names are: || J k CI same compound enantiomers diastereomers constitutional isomers not isomeric Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3S)-2,3-dichloropentane Compound I: (2S, 3S)-2,3-dichloropentane, Compound II: (2S, 3S)-2,3-dichloropentane Compound I: (2S, 3R)-2,3-dichloropentane, Compound II: (2S, 3R)-2,3-dichloropentane Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3R)-2,3-dichloropentanearrow_forward
- What is the stereochemistry of this compound? 2E, 5E 2Z, 5Z 2Z, 5E 2E, 5Zarrow_forward8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomersarrow_forward(a) (1R,2R)-1,2-dibromocyclohexane, label each structure you have drawn as chiral or achiral.arrow_forward
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