Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 5.10A, Problem 5.17P
Draw a Fischer projection for each compound. Remember that the cross represents an asymmetric carbon atom, and the carbon chain should be along the vertical, with the IUPAC numbering from top to bottom.
- a. (S)-propane-1,2-
diol - b. (R)-2-bromobutan 1-ol
- c. (S)-1,2-dibromobutane
- d. (R)-butan-2-ol
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Classify each compound as IDENTICAL to A or an ENANTIOMER to A.
1. Draw the two conformations of trans-1-bromo-3-methylcyclohexane using both the Newman
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conformers will be present at equilibrium?
2. Draw a structure of a chiral alcohol.
• Question 5: Label each stereogenic center as R or S.
CH₂
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b. CH
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CH₂CH₂
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C.
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CI
CH3
d. Br C
ICH₂
H
e.
f.
H*
HO
C
HOOC
CH₂
HO
CH(CH3)2
-C₂
C
CH3
SH
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H
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g.
h.
.CI
CI
Chapter 5 Solutions
Organic Chemistry (9th Edition)
Ch. 5.2 - Determine whether the following objects are chiral...Ch. 5.2A - Prob. 5.2PCh. 5.2B - Prob. 5.3PCh. 5.2B - Prob. 5.4PCh. 5.2C - Prob. 5.5PCh. 5.3 - Prob. 5.6PCh. 5.3 - Prob. 5.7PCh. 5.4D - Prob. 5.8PCh. 5.4D - Prob. 5.9PCh. 5.4D - Prob. 5.10P
Ch. 5.5 - Prob. 5.11PCh. 5.7 - When optically pure (R)-2-bromobutane is heated...Ch. 5.7 - Prob. 5.13PCh. 5.8 - Prob. 5.14PCh. 5.9B - Draw three-dimensional representations of the...Ch. 5.10A - For each sot of examples, make a model of the...Ch. 5.10A - Draw a Fischer projection for each compound....Ch. 5.10B - Prob. 5.18PCh. 5.10C - For each Fischer projection, label each asymmetric...Ch. 5.11C - Prob. 5.20PCh. 5.13 - Prob. 5.21PCh. 5.13 - Prob. 5.22PCh. 5.15 - Prob. 5.23PCh. 5.16A - Prob. 5.24PCh. 5 - The following four structures are naturally...Ch. 5 - For each structure, 1. star () any asymmetric...Ch. 5 - Prob. 5.27SPCh. 5 - Prob. 5.28SPCh. 5 - Prob. 5.29SPCh. 5 - Prob. 5.30SPCh. 5 - Prob. 5.31SPCh. 5 - Prob. 5.32SPCh. 5 - Prob. 5.33SPCh. 5 - Prob. 5.34SPCh. 5 - For each structure, 1. draw all the stereoisomers....Ch. 5 - Prob. 5.36SPCh. 5 - Prob. 5.37SPCh. 5 - 3,4-Dimethylpent-1-ene has the formula...Ch. 5 - A graduate student was studying enzymatic...Ch. 5 - Prob. 5.40SPCh. 5 - Prob. 5.41SP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Glucose 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_forward4. Draw enantiomers for each of the following compounds using Fischer projections and skeletal structures with dash-wedge notation. bavogmos simsa A. B. C. CH3 FO Br F OH CH3 .0arrow_forwardClassify each compound as identical to A or its enantiomer. CHO CHO H OH CHO a. CH,CH-C--OH CumCH,CH3 H OH b. d. HO C. ČH,CH3 н он CH;CH CHO CHO Aarrow_forward
- Aa.121.arrow_forward6. Indicate whether the circled carbon in each of these is chiral a. CH3-CH-CH2-CH3 b. CH3-CH2-C-CH3 Cl c. CH3-CH2-CH-OH d. Br CH2 ©H H,C CH2 CH3 HC. CH2 Br CHarrow_forwardUsing the cyclohexane with the C’s numbered as shown, draw a chair form that fits each description. a. The ring has an axial CH3 group at C1 and an equatorial OH on C2. b. The ring has an equatorial CH3 group on C6 and an axial OH group on C4. c. The ring has equatorial OH groups on C1, C2, and C5.arrow_forward
- 3.A carbon atom that is bonded to four different groups is a/an A.achiral center B.chirality center C.symmetrical center D.symmetrical centerarrow_forwardDraw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description. a.a 1,1-disubstituted cyclohexane with an axial CH3CH2 group b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 group.arrow_forwardDraw a chair conformation of cyclohexane with one CH3CH2 group and one CH3 group that fits each description. a. a 1,1-disubstituted cyclohexane with an axial CH3CH2 group b. a cis-1,2-disubstituted cyclohexane with an axial CH3 group c. a trans-1,3-disubstituted cyclohexane with an equatorial CH3 group d. a trans-1,4-disubstituted cyclohexane with an equatorial CH3CH2 grouparrow_forward
- 3. Construct models of 2,3-dibromobutane. Construct as many stereoisomers as possible. (How many stereoisomers are possible?) Label each stereogenic center. a. Draw 3-D (wedge) structures of each stereoisomer. b. Draw Side-view projections of each stereoisomer. Draw Newman projections of each stereoisomer. d. Draw Fischer projections of each stereoisomer. C.arrow_forward6. The name of the compound at the right represented CH2CH3 in a Fischer projection is- A) (R)-3-methylhexane B) (S)-3-methylhexane CH 3 -H C) (R)-4-methylhexane D) (S)-4-methylhexane E) (R)-2-ethylpentane CH2CH2CH3 7. The two molecules on the right are- H H H A) enantiomers B) diastereomers C) atropisomers D) structural isomers E) identical Br Br H Br Br Tarrow_forwardConsider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?arrow_forward
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