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 19PP
Interpretation Introduction
Interpretation:
The relation between the pairs 1 and 4, 2 and 3, and 2 and 4 are to be determined. The physical properties that are similar between pairs 1 and 3 are to be predicted.
Concept introduction:
Stereoisomers that are not mirror images of each other are diastereomers.
Diastereomers have different physical properties, such as different solubilities, different melting points, different boiling points, and so on.
Stereoisomers that are mirror images of each other are enantiomers.
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Students have asked these similar questions
(a) All Isomers have the same molecular formulae. Explain this further. Hint what does it mean to
have the same molecular formulae?
(b) What is Constitutional (structural) isomerism? Hint, isomers are different, so what is different
between a pair of constitutional isomers (see the chart on the last page for examples).
(c) What is Conformational isomerism?
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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- (a) Is the compound CH3CH≡CH2 saturated or unsaturated?Explain. (b) What is wrong with the formulaCH3CH2CH≡CH3?arrow_forward5.76 2,3-Dibromoprop-1-ene (C3H4Br₂) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule with the formula C3H3Br₂Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br₂Cl; (b) enantiomers of C3H3Br₂Cl; (c) diastereomers of C3H3Br₂Cl. co 11 HHH Juods H Brugtrio 2 bas A 2,3-Dil so ontemme A chon Br 2,3-Dibromoprop-1-enearrow_forwardThere are four dimethylcyclopropane isomers. (a) Write three-dimensional formulas for these isomers. (b) Which of the isomers are chiral? (c) If a mixture consisting of 1 mol of each of these isomers were subjected to simple gas chromatography, how many fractions would be obtained and which compounds would each fraction contain? (d) How many of these fractions would be optically active? tod o ors brie page 10 of 17arrow_forward
- (a) which if the structure of trans-1,2-dimethylcyclopentane? (b) which is the most stable conformation of 1-bromo-2-ethylcyclohexane? (c) which is the least stable conformation of 1-bromo-2-ethylcyclohexane? (d) which is the more stable configuration of 1,3-dimethylcyclopentane? *Et = ethylarrow_forwardWhich statements are true about constitutional isomers? (a) They have the same molecular formula. (b) They have the same molecular weight. (c) They have the same order of attachment of atoms. (d) They have the same physical propertiesarrow_forward(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.arrow_forward
- (a) Draw the nine isomers having the formula C7H16 . (Hint: There is one structure with a seven-carbon chain, two structures with six-carbon chains [one is illustrated in the margin above], five structures with a five-carbon chain, and one structure with a fourcarbon chain.)(b) Identify the isomers of C7H16 that are chiral.arrow_forwardExplain why (i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride. (ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.arrow_forward4. (a) Draw all possible isomers of C4H3CI2. (b) Indicate which pairs of compounds are enantiomers of one another. (c) Indicate which pairs of compounds are diastereomers of one another. (d) Indicate which compounds would have optical rotations of 0°. (e) Assign R and S configurations to all chirality centers of the compounds in part (a).arrow_forward
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