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 4PP
Interpretation Introduction
Interpretation:
The three-dimensional formulas for both enantiomers of the molecules with chiral centers are to be written.
Concept introduction:
Chiral centers are tetrahedral atoms that have four different substituents.
Each chiral center will be either
Enantiomers are one of the stereoisomers that are mirror images of each other that are non-superimposable.
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Students have asked these similar questions
2. Some of the
molecules listed here
have a center of
chirality. Write the
Fischer
projection
structures of both
enantiomers
for
molecules that have a
center of chirality.
(a) 2-Fluoropropane
(b) 2-Methylbutane
(e) 2-Chlorobutane
(d) 2-Methyl-1-
butanol
(e) trans-2-Butene
(f) 2-Bromopentane
(g) 3-Methylpentane
(h) 3-Methylhexane
(1) 2-Methyl-2-pentene
(i) 1-Chloro-2-
methylbutane
If either of the following molecules has a stereogenic carbon (chirality center), give structures for both of the enantiomers.
(a) 2-bromopropane (b) 2-bromobutane
(a) Write the structures of the following compounds and mark them as chiral
or achiral. 4
(i) 2-Bromopentane (ii) 3-Bromopentane
(iii) 1-Bromo-2-methylbutane (iv) 2-Chloro-3-methylbutane
(b) Identify the asymmetric carbon in the chiral compounds.
(c) Write the structure of the other enantiomer of the chiral compounds.
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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- d) Identify one compound that is expected to have identical physical properties as structure II. (e) Other than structures III and VI, identify a stereoisomer with a different boiling point from that of structure II. (f) Other than structures IV, identify one diastereomer of structure I. (g) How many stereoisomers may be derived from structure V?arrow_forwardDraw 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. (a) ОН (b) (c) NH, ОН СH—CH—СООН | pentan-2-ol pentan-3-ol alanine (d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane (h) (i) H CH; "H H. H CH, Harrow_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
- (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_forwardDraw one of each pair of enantiomers or diastereomers for each of the following compounds using a perspective formula (dash-wedge). You must indicate the points of stereochemistry (E, Z, R, S) plus locant numbers. State if no stereoisomers are possible. Write your answer in the blank space .(a) 1-bromo-2-chlorocyclohexane (b) 2-bromo-4-methylpentane(c) 2-bromo-4-chloropentane (d) 1,3-dibromo-4,6-dimethyl-3-octenearrow_forward(a) Draw all the stereoisomers of 2,3,4-tribromopentane. (Using Fischer projections may be Q2: If you think you know your definitions, try this difficult problem. helpful.) You should find two meso structures and one pair of enantiomers. (b) Star (*) the asymmetric carbon atoms, and label each as (R) or (5). (c) In the meso structures, show how C3 is pot asymmetric, nor is it a chiral center, yet it is a stereocenter. (d) In the enantiomers, show how C3 is not a stereocenter.arrow_forward
- Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forwarda) Considering compounds 2a through 21, identify: ONE PAIR of geometric isomers; TWO PAIRS of enantiomers and THREE PAIRS of identical molecules. b) Give the names, including the configurations, of each of the geometric isomers and of each of the enantiomers. Draw the relevant structures in the space provided in the Answer Booklet. c) Sort compounds 2a, 2b, 2c, 2f and 2k in order of increasing solubility in water and briefly justify your ordering. 2 НО. AH H H anulta HOwno barwolset of ef 28nuor OH 2bc 2c ning) bi 10291 H WH 2 st brbot di OH Lacenoqoid OH to nabio ni one nt at dit st 2e OH "H OH bre 2a 2d 2g 2j H HO 2h 2k HO ...H di al nt o 2f 2i 21arrow_forward12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?arrow_forward
- 2A2: Apply the concepts of stereocenters, chirality, asymmetry, and the CIP Rules to label enantiomers/ diastereomers and R/S or E/Z absolute configurations. These two (2) structures have ambiguous configurations. Provide a wedge and dash structure for the indicated configurational isomer. In your response, keep the overall structural orientation the same as given. In addition, label all alkenyl FGs as either E or Z in both structures by showing your work. & H3 C CH3 (R, R, R,) H3CO. H3CO CH3 (S, S, S) CH3 OCH 3 OCH 3arrow_forward5:51 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 Sarrow_forward• PRACTICE PROBLEM 6.6 S 2 reactions that involve substitution at a chirality center can be used to relate the configuration of one molecule to another, because we know the SN2 reaction will occur with inversion. (a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane enantiomers based on the following data. [The configuration of (-)-2-butanol is given in Section 5.8C.] HO- (+)-2-Chlorobutane (-)-2-Butanol SN2 [a]3 = +36.00 (Enantiomerically pure) [a] = -13.52 (Enantiomerically pure) noin (b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassium iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minus optical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutane?arrow_forward
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