Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 5.SE, Problem 36AP
Interpretation Introduction
Interpretation:
The chirality centre of Erythronolide B is to be explained.
Concept introduction:
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Iejimalide B, an anticancer agent with a 24-membered ring, is isolated from a tunicate found off Ie Island in Okinawa. (a) Label each double bond in iejimalide B as E or Z. (b) Label each tetrahedral stereogenic center as R or S. (c) How many stereoisomers are possible for iejimalide B?
lejimalide B, an anticancer agent with a 24-membered ring, is isolated from a tunicate found off le Island in Okinawa. (a) Label
each double bond in iejimalide B as E or Z. (b) Label each tetrahedral stereogenic center as R or S. (c) How many stereoisomers
are possible for iejimalide B?
CH;0
CHO
OCH,
HO,
iejimalide B
Paroxetine (Paxil) is an antidepressant that is a member of a family of drugs known
as Selective Serotonin Reuptake Inhibitors (SSRIS). This family of drugs also includes
fluoxetine (Prozac) and sertraline (Zoloft). SSRIS work by inhibiting the reuptake of
the neurotransmitter serotonin in the synapses of the central nervous system follow-
ing release of serotonin during excitation of individual nerve cells. Between firings, the
serotonin is taken back up by a nerve cell in preparation for firing again. Inhibition of
reuptake has the effect of increasing the time serotonin molecules remain in the syn-
apses following excitation, leading to a therapeutic effect. In one synthesis of parox-
etine, the following reagents are used. Draw the structures of synthetic intermediates A
and B.
F
НО
SOCI,
A
B
HO
Pyridine
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- ribavirin an antiviral agent used againt hepatits c and viral pneumonia contains a 1, 2,4 traizole ring why is the ring aromaticarrow_forwardCan i get help with problem?arrow_forwardAziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiflu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.arrow_forward
- Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.arrow_forwardHow many stereoisomers are possible for 5-hydroxyhexanal?arrow_forwardIs amitriptyline chiral? If so, how many of the possible stereoisomers are formed in this synthesis?arrow_forward
- Draw the structure of (S,S)-ethambutol, a drug used to treat tuberculosisthat is 10 times more potent than any of its other stereoisomers. (See attached)arrow_forwardWhat product is formed when 2-acetylcyclopentanone is treated withNaOCH2CH3, followed by CH3I?arrow_forwardIs clozapine chiral? If so, how many of the possible stereoisomers are formed in this synthesis?arrow_forward
- Draw a stepwise mechanism for the following reaction, one step in the synthesis of the cholesterol-lowering drug pitavastatin, marketed in Japan as a calcium salt under the name Livalo.arrow_forwardCompound X has the molecular formula C10H12O. The IR spectrum of X has a strong band near 1710 cm-1. Compound X forms a phenyhydrazone, but gives a negative Tollens’ test and a positive iodoform test. What is the structure of the compound?arrow_forwardBongkrekic acid is a toxic compound producted by Pseudomonas cocovenenans, and isolated from a mold that grows on bongkrek, a fermented Indonesian coconut dish. In bongkrekic acid, abel each double bond as E or Z and each tetrahedral stereogenic center as R or S. Labels: E ZR СООН bongkrekic acid COOH H3C H3CO СООНarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning