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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- Identify the stereochemical configuration of this cyclic compound. CI R Osarrow_forwardFollowing is an outline of a synthesis of the bronchodilator carbuterol, a beta-2 adrenergic blocker with high selectivity for airway smooth muscle receptors. Q. Is carbuterol chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardNH2 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_forward
- Salinosporamide A, isolated from a microbe called Salinispora tropica has shown promise as an inhibitor of cancer cell growth. Select the chiral centers in the following structure; the selected centers will appear highlighted green.arrow_forwardA 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_forward
- Consider the chirality center in the compound shown. What is the highest priority substituent group? O-(CH₂)₂CC13 O-(CH₂)3CH(CH3)2 O-C(OH)₂CH₂CH₂ O -(CH₂)₂ Br What is the second highest priority substituent group? O-(CH₂)₂CC1₂ O -C(OH)₂CH₂CH₂ O-(CH,),CH(CH,), O-(CH₂)₂ Br Br CI CI CI HO OHarrow_forwardHiiiarrow_forwardHow many chirality centers does this molecule have?arrow_forward
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