Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 5, Problem 6PP
Interpretation Introduction
Interpretation:
The number of chiral carbon atoms in the given compound is to be shown.
Concept introduction:
A carbon having four different group is called chiral center.
A chiral molecule is non-superimposable on its mirror image.
In chiral molecules, an asymmetric carbon atom is present.
If multiple bonds are present, the carbon atom will not be considered as a chiral carbon.
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Students have asked these similar questions
Which of the following compounds are chiral? Which, if any, are meso? Which, if any,
does not have a possible diastereomer?
(a)
(b)
(c)
(d)
Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain
parasites
(Org. Lett. 2012, 14, 3878-3881):
(a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B.
(b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL
LETTER of your choice.
A. 2
В. 4
С. 8
D.
16
ANSWERS:
(a) A.
В.
C.
(b)
5:51
Draw examples of the following:
(a) A meso compound with the formula C8H18
(b) A meso compound with the formula C9H20
(c) A compound with two chirality centers, one R and the other S
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 1PPCh. 5 - Prob. 2PPCh. 5 - Prob. 3PPCh. 5 - Prob. 4PPCh. 5 - Prob. 5PPCh. 5 - Prob. 6PPCh. 5 - Prob. 7PPCh. 5 - Practice Problem 5.8 Write three-dimensional...Ch. 5 - Prob. 9PPCh. 5 - Prob. 10PP
Ch. 5 - Practice Problem 5.11 List the substituents in...Ch. 5 - Prob. 12PPCh. 5 - Practice Problem 5.13 Tell whether the two...Ch. 5 - Prob. 14PPCh. 5 - Prob. 15PPCh. 5 - Prob. 16PPCh. 5 - Prob. 17PPCh. 5 - Prob. 18PPCh. 5 - Prob. 19PPCh. 5 - Prob. 20PPCh. 5 - Practice Problem 5.21 The following are formulas...Ch. 5 - Practice Problem 5.22 Write three-dimensional...Ch. 5 - Prob. 23PPCh. 5 - Practice Problem 5.24 Give names chat include (R)...Ch. 5 - Prob. 25PPCh. 5 - Prob. 26PPCh. 5 - Prob. 27PPCh. 5 - Prob. 28PPCh. 5 - Practice Problem 5.29 Write formulas for all of...Ch. 5 - Prob. 30PPCh. 5 - Prob. 31PPCh. 5 - Prob. 32PPCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - 5.35 Designate the (R) or (S) configuration at...Ch. 5 - Prob. 36PCh. 5 - (a) Write the structure of...Ch. 5 - Shown below are Newman projection formulas for...Ch. 5 - 5.39 Write appropriate structural formulas...Ch. 5 - Discuss whether each of the following compounds...Ch. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Compound F has the molecular formula C5H8 and is...Ch. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - For the following molecule, draw its enantiomer as...Ch. 5 - 5.49 (Use models to solve this...Ch. 5 - 5.50 (Use models to solve this...Ch. 5 - (Use models co solve this problem.) Write...Ch. 5 - 5.52 Tartaric acid was an important compound in...Ch. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 1LGPCh. 5 - Prob. 2LGPCh. 5 - Prob. 3LGP
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- (A) How many chirality centers does the following molecule contain? (B) How many stereoisomers are possible for this molecule? (C) Assign R,S designation to each chiral carbonarrow_forwardOnly one of these compounds can be described as non-conjugated. a) b)arrow_forwardAssign the stereogenic centers in the molecule with the asterisk (i) (ii) Assign priority or preference of the groups attached to the chirality center (stereogenic center) (iii) (iv) (v) Describe the chirality centers using R and/or S descriptors Name the compound Write the structural formula of the enantiomer.arrow_forward
- 7.(a) Draw and label (a) the enantiomer and (b) a pair of diasteromers of the following compound. OH (c) Will a 50:50 mix of the enantiomers of the compound be optically active (rotate plane polarized light). Explain the reason for your answer d) Will a 50:50 mix of the two diasteriomers you drew in (c) be optically active (rotate plane polarized light). Explain the reason for your answerarrow_forward5.40 Consider the following pairs of structures. Designate cach chirality center as (R) or (S) and identify the relationship bêtween them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers. Br CH, H,C Br (a) () and and ĆI CI H. CH H,C H CH3 CH3 (b) and F Br Br F CI CI -H- (k) H- and CH, Br CH, Br H. -CI H- CI (c) H,CH and F CH3 CH3 CH3 Br H,C H. Br H- (1) -CI Br- CH3 and HH CI- Br (d) F CH, H and Fu CH3 Hi Br CH, H,C CH3 F H Br (m) and (e) H,C and "F HC H Br H. CH Br and (n) and CH3 CI (0) and CH3 Br H,CC. Br and Ci Ci CI CI (h) Cl- and -CI (p) and ČI ČI CI Ci CI Br and (q) Br Br C=C=CH C=Cc=CBr and ČI CI HICarrow_forward(a) Distinguish between:(i) C6H5— COCH3 and C6H5— CHO(ii) CH3COOH and HCOOH(b) Arrange the following in the increasing order of their boiling points:CH3CHO, CH3COOH, CH3CH2OHarrow_forward
- a）Draw all other stereoisomers of the molecule, labelling meso forms (if any), and assign descriptors to chiral carbon atoms. (b) Including molecule, label pairs of enantiomers and pairs of diastereomers. (c) If you were to distill a mixture of all the isomers, how many fractions could be obtained, and what would in each fraction?arrow_forwardBoth enantiomers of α-terpineneol may be isolated from various natural sources: the (S) isomer is a constituent of longleaf pine oil, whereas the (R) isomer is present in the petitgrain oil. Change the following depiction of α-terpineneol to represent the structure of (S)-α-terpineneolarrow_forwardIdentify the specific type of relationship between each of the following pairs of molecules (i.e., either same, constitutional isomers, enantiomers, diastereomers, conformers, or unrelated). (a) (b) (c) (d) (e) H. H CH3 H3C Lon, maf_* Lon, (f) Br (g) Br Br (h) Br H. LCH3 H H H H LaCH3 H3C LCH3 H H3C" CI H. Br C, CH CH3 CI CI H CI H. Brarrow_forward
- A limited number of chiral compounds having no stereogenic centersexist. For example, although A is achiral, constitutional isomer B ischiral. Make models and explain this observation. Compoundscontaining two double bonds that share a single carbon atom are calledallenes. Locate the allene in the antibiotic mycomycin and decidewhether mycomycin is chiral or achiral.arrow_forward(c) Answer the following questions: It is possible for a compound to be chiral even though it lacks a carbon atom with four different groups. Using two nitro groups, one isopropyl group and one carboxy group as substituents, draw the structure of an optically active biphenyl that is void of a chiral carbon. i. ii. Deduce, giving reasons, whether or not the following molecules are optically active. H3C CH3 ČH(CH3)2 Quaternary ammonium salt NH2 Compound A НОСІНС OCH3 OCH3 Br Compound Barrow_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_forward
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