Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 5.6, Problem 13P
One of the following molecules (a)–(d) is d-erythrose 4-phosphate, an intermediate in the Calvin photosynthetic cycle by which plants incorporate CO2 into carbohydrates. If d-erythrose 4-phosphate has R stereochemistry at both chirality centers, which of the structures is it? Which of the remaining three structures is the enantiomer of d-erythrose 4-phosphate, and which are diastereomers?
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(a) assign R or S configuration to each chiral center,
(b) Which compound are enantiomers?
(c) Which compounds are diastereomers?
In the molecules below
(a) H
(b) O
H-C-OH
HO-C-H
H-C-OH
HO-C-H
HO-C-H
HO-C-H
H-C-OH
-CIO
CH,OPo,
CH,OPO,
CH,OPO,
CHOPO,
Which molecule is the enantiomer of molecule a?
which molecule is a diasteromer of molecule b?
Which answer describes the relationship between these compounds?
(a)
OH
H
OH
H
(b)
H
O They are the same molecule.
Enantiomers
Diastereomers
Both Meso
OH
OH
H
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
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- 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 Sarrow_forwardWhich is the enantiomer of this molecule? NH2 (A) (C) B NH2 デ NH2 H- さ NH, (B) (D) H2N- Harrow_forwardWhich of the following compounds are chiral? Draw them, and label the chirality centers. (a) 2, 4-Dimethylheptane (b) 5-Ethyl-3, 3-dimethylheptane (c) cis-1, 4-Dichlorocyclohexanearrow_forward
- 9. What is the relationship between the following molecules? (A) (B) ê ê ® Enantiomers Diastereoisomers Conformational isomers Structural isomers No isomeric relationship I CO₂H II CO,Harrow_forwardFollowing are stereorepresentations for the four stereoisomers of 3-chloro-2-butanol. (a) Assign an R or S configuration to each chiral center. (b) Which compounds are enantiomers? (c) Which compound are diastereomers?arrow_forwardWhich compounds contain chiral centers? (a) 2-Chloropentane (b) 3-Chloropentane (c) 3- Chloro-1-pentene (d) 1,2-Dichloropropanearrow_forward
- OH A B NH2 NH2 Which labelled carbon (A or B) is chiral? (A) B B) Aarrow_forward(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_forwardWhich of the following compounds is optically active? Explain your answer. (C4) Cl,C=CH(CH,) NH,CHCOOH (CH,),C(NH, )COOH CH(CH,), A вarrow_forward
- Which of the two is chiral? 1,2,4,5-tetramethylcyclohexane or 2-hydroxypropanoic acidarrow_forwardDraw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forwardTreatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forward
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