Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 5, Problem 5.7P
The facts in section 5.4A can be used to locate stereogenic centers in any molecule, no matter how complicated. Always look for carbons surrounded by four different groups. With this in mind, locate the four stereogenic centers in aliskiren, a drug introduced in
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2. The molecules shown below are four terpineol isomers. They are
isolated from plants and have distinct aromas. For example, a -terpineol
is a common perfume ingredient and smells similar to lilacs.
Hol
H-O-
a-terpineol
B-terpineol
Y-terpineol
4-terpineol
A) Draw a structural isomer of terpineol that meet the following criteria. You should draw one unique structure for each set. You
must draw each molecule twice, once as a skeletal structure and once as a complete Lewis structure showing all atoms, bonds,
and lone pairs of electrons.
i. Does not have a ring.
ii. Has an E alkene.
iii. Has a secondary alcohol.
iv. Does not contain an alcohol.
B) Draw a complete Lewis structure of a-terpineol showing all bonds, atoms and lone pairs of electrons.
Q1:- Which of the isomeric alcohols having formula CSH120 are chiral ? Which are achiral? Draw the
enantiomers.
Q2:- Which of the following compounds are chiral? Draw the stereo structures.
a- 1-Chloro-2-bromobutane
b- 1,2-Dichloro-3-methyibutane
What is the name for a 50:50 mixture of enantiomers such as a 50:50 mixture of (S)-2-
butanol and (R)-2-butanol? Conformers, racemic, diastereomers, meso, different, stereopure,
chiral, optically active
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Draw the mirror image of each compound. Label each...Ch. 5 - Prob. 5.4PCh. 5 - A molecule is achiral if it has a plane of...Ch. 5 - Problem 5.6 Locate the stereogenic centers in each...Ch. 5 - The facts in section 5.4A can be used to locate...Ch. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Label each compound as R or S.Ch. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Problem 5.18 Compounds E and F are two isomers of...Ch. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Which of the following cyclic molecules are meso...Ch. 5 - Prob. 5.26PCh. 5 - Prob. 5.27PCh. 5 - Problem 5.28 The amino acid has the physical...Ch. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Prob. 5.38PCh. 5 - Prob. 5.39PCh. 5 - 5.40 Determine if each compound is identical to or...Ch. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Prob. 5.46PCh. 5 - Label each stereogenic center as R or S. a. c. e....Ch. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.52PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Prob. 5.56PCh. 5 - Prob. 5.57PCh. 5 - Prob. 5.58PCh. 5 - 5.59 Explain each statement by referring to...Ch. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 - Prob. 5.66PCh. 5 -
5.67 Artemisinin and mefloquine are widely used...Ch. 5 - 5.68 Saquinavir (trade name Invirase) is a...Ch. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Prob. 5.72PCh. 5 - Problem 5.73 An acid-base reaction of with a...
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- Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you. 1-bromo-2-methylbutanearrow_forwardFill in the boxes with the correct organic structure. You must show relative stereochemistry where necessary. You only need to draw one enantiomer if the product is a racemic mixture. 1. OsO4 2. NaHSO3 MCPBA HglO6 1. NaOH 2. HCIarrow_forwardIndicate whether the pair of structures shown represent stereoisomers, constitutional isomers, different conformations of the same compound, or the same conformation of a compound viewed from a different perspective. Note that cis, trans isomers are an example of stereoisomers. CH3 CI- CH3 CH3- H3C- CH3- 오. CH3 ♦arrow_forward
- Indicate whether the pair of structures shown represent stereoisomers, constitutional isomers, different conformations of the same compound, or the same conformation of a compound viewed from a different perspective. Note that cis, trans isomers are an example of stereoisomers. CH₂CH3 -CH₂CH3 H₂N. CH₂CH3 -NH₂ CH₂CH3 H₂N- NH₂arrow_forward1) What are isomers of haxane.Arrange the isomers in order of increasing boiling points.arrow_forward1a. How many stereogenic centers are present in the structure below? Indicate them with asterisk(s). How many stereoisomers are possible? # of stereogenic centers: # of possible stereoisomers:arrow_forward
- The shrub ma huang (Section 5.4A) contains two biologically active stereoisomers—ephedrine and pseudoephedrine—with two stereogenic centers as shown in the given structure. Ephedrine is one component of a once-popular combination drug used by body builders to increase energy and alertness, whereas pseudoephedrine is a nasal decongestant. a.Draw the structure of naturally occurring (−)-ephedrine, which has the 1R,2S configuration. b.Draw the structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration. c.How are ephedrine and pseudoephedrine related? d.Draw all other stereoisomers of (−)-ephedrine and (+)pseudoephedrine, and give the R,S designation for all stereogenic centers. e.How is each compound drawn in part (d) related to (−)-ephedrine?arrow_forwardCalculate the number of degrees of unsaturation for each molecular formula.a. C6H6b. C40H56c. C10H16O2d. C8H9Bre. C8H9CIOf. C7H11Ng. C4H8BrNh. C10H18CINOarrow_forwardHow are compounds I and II related? "Compound I" "Compound II" O They are different conformations of the same compound. O They are constitutional isomers. O They are cis-trans isomers. O They are completely different compounds with different formulas. ○ They are a pair of diastereoisomers. O They are a pair of enantiomers.arrow_forward
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