ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
6th Edition
ISBN: 9780072397475
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 15, Problem 25P
a. Draw the 14 constitutional isomers of molecular formula
b. Name all compounds that contain a trisubstituted benzene ring.
c. For which compound(s) are stereoisomers possible? Draw all possible stereoisomers.
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a. Draw the 14 constitutional isomers of molecular formula C8H9Cl that contain a benzene ring.
b.Name all compounds that contain a trisubstituted benzene ring.
c.For which compound(s) are stereoisomers possible? Draw all possible stereoisomers.
1a. How many stereogenic centers are present 1c. Draw a three-dimensional structure of a
in the structure below? Indicate them with
asterisk(s). How many stereoisomers
stereoisomers are
possible?
chiral compound with the molecular formula
of C4H4Cl₂ that does not have a stereogenic
carbon. In addition, draw the enantiomer of
this compound.
Number of stereogenic centers:
Number of stereoisomers possible:
1b. Draw one of the two most stable
stereoisomers of the compound in 1a using a
planar structure with wedges and dashes. Now
draw it in its preferred chair conformation.
1d. Draw two meso compounds with the
molecular formula of C7H14.
Part D. Do the two structures A and B of each pair drawn below represent the same molecule,
constitutional isomers, or stereoisomers? If A and B are stereoisomers, further classify them as
enantiomers or diastereomers.
H3C
Structure A
H3C
HO
H3C
H3C
Br
T
H
H3C
H
HO
H3CC
H
C
Br
HC
H
H
H
H
CH₂Br
CH₂CH3
H
CH₂CH3
CH₂OH
OH
H HO
G
G
H HO
H HO
G
CH3
CH3
CH3
Br
Hallo
H
H3C
H
Structure B
H3C
CH3
Br
WING
H
Br
HOCH₂
CH3
CH3
HO
H
CH₂OH
H
CH₂CH3
H
CH₂CH3
H
H
H
H
H
H
Gim
CH3 H
OH
"H
·GII.
CH3
HO.
OH
OH
CH3
CH3
OH
Relationship of A and B
Chapter 15 Solutions
ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
Ch. 15.2 - Prob. 1PCh. 15.2 - Problem 17.2 What orbitals are used to form the...Ch. 15.3 - Prob. 4PCh. 15.3 - Problem-17.5 What is the structure of propofol,...Ch. 15.6 - Prob. 7PCh. 15.8 - Prob. 8PCh. 15.8 - Prob. 11PCh. 15.8 - Prob. 12PCh. 15.8 - Problem 17.16 Rank the following compounds in...Ch. 15.8 - Problem 17.17 Draw the seven resonance structures...
Ch. 15 - 17.23 Name each compound and state how many lines...Ch. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 15 - 17.28 Draw a structure corresponding to each...Ch. 15 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - 17.38
How many electrons does C contain?
How...Ch. 15 - Prob. 36PCh. 15 - 17.40 Explain the observed rate of reactivity of...Ch. 15 - 17.41 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 39PCh. 15 - 17.43 Draw additional resonance structures for...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 17.46 Which compound in each pair is the stronger...Ch. 15 - 17.47 Treatment of indene with forms its...Ch. 15 - Prob. 45PCh. 15 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 15 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - 17.53 How many signals does each compound...Ch. 15 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 15 - 17.55 Propose a structure consistent with each...Ch. 15 - 17.56 Propose a structure consistent with each...Ch. 15 - 17.57 Thymol (molecular formula ) is the major...Ch. 15 - 17.58 You have a sample of a compound of molecular...Ch. 15 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 15 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 15 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 15 - 17.62 Answer the following questions about...Ch. 15 - 17.63 Stanozolol is an anabolic steroid that...Ch. 15 - Prob. 61P
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- What is true about the relationship between the following compounds? CH3 CH3 CH; CH; CH3 CH3 A В O All three are stereoisomers of each other. OA and B are the same compound while C is a stereoisomer. All three are the same compound. A and B are the same while C is a conformer, all of the same compound . O A and C are the same while B is a stereoisomer.arrow_forwardConsider the compound below. a) Draw the structure showing stereochemistry, in which carbon 1 has S configuration and carbon 2 has R configuration. b) Draw the structure showing stereochemistry, in which carbons 1 and 2 have S configuration. c) are the two structures from part a and b diastereomers, identical, enantiomers, or unrelated?arrow_forward10. What is the relationship between the following two compounds? (see attached screenshot). a. constitutional isomers b. stereoisomers c. identical d. not isomers; different compounds entirelyarrow_forward
- 5. Give the stereochemical relationship between each pair of isomers. Examples are same compound (meso), constitutional isomers, enantiomers, and diastereomers. H3C CH3 HO OH lll a. Но OH H Br CH3 b. C/ H3C CI H. ICH3 CH3 с. CH3 H. CH3 d. Но. H3C OH CH2OH Ho CH2OH Br e. Br H3C f. H CH3 H3C CH3arrow_forwardClassify each compound as identical to A or its enantiomer.arrow_forwardDraw the three constitutional isomers having molecular formula C7H14 that contain a five-membered ring and two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw the two stereoisomers.arrow_forward
- Part D. Do the two structures A and B of each pair drawn below represent the same molecule, constitutional isomers, or stereoisomers? If A and B are stereoisomers, further classify them as enantiomers or diastereomers.arrow_forwardGlucose is a simple sugar with five substituents bonded to a sixmembered ring.a.Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring. b.Convert this representation to one that uses a hexagon with wedges and dashed wedges. c.Draw a constitutional isomer of glucose. d.Draw a stereoisomer that has an axial OH group on one carbon.arrow_forward#23arrow_forward
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