Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 3.12C, Problem 3.20P
Interpretation Introduction
Interpretation: The information regarding the stability of
Concept introduction: Cis-trans isomerism determines the position of position of different groups relative to each other. If the different groups points in the same direction then they are said to be cis with respect to each other but if they point in the opposite direction then they are trans with respect to each other.
To draw: The structures representing the stability of
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Rings + Unsaturation --- Hydrogenation
If compound A C51H81BrN5O3P3 is hydrogenated to give compound B C51H101BrN5O3P3. How many rings does compound A have? Assume that P has a valency of 5.
Would the answer be 4 rings?
Formula -> unsat + rings = 1+C +N/2 - H/2 - X/2
For centuries, Chinese herbal medicine has used extracts of Ephedra sinica to treat asthma.
Ephedra as an"herbal supplement" has been implicated in the deaths of several athletes
and has recently been banned as a dietary supplement. Phytochemical investigation of
this plant resulted in isolation of ephedrine, a very potent dilator of the air passages of
the lungs. Ephedrine also has profound effects on the cardiovascular system. The natu-
rally occurring stereoisomer is levorotatory and has the following structure. Assign an
Ror S configuration to each chiral center.
H
NHCH3
Ephedra sinica, the source
of ephedrine, a potent
bronchodilator.
HO
H
CH3
Ephedrine [a -41
CH3
H3C
N-
-CH2
H2C CH2
H3C
(1)
CH3
CH3
CH3
H2
Br
CH3
CH2
ČH3
(2)
CH
HC
CH
CH
Chapter 3 Solutions
Organic Chemistry (9th Edition)
Ch. 3.2 - Using the general molecular formula for alkanes:...Ch. 3.3B - Name the following alkanes and haloalkanes. When...Ch. 3.3B - Write structures for the following compounds. a....Ch. 3.3B - Provide IUPAC names for the following compounds....Ch. 3.3B - Prob. 3.5PCh. 3.3B - Prob. 3.6PCh. 3.3B - Prob. 3.7PCh. 3.3B - Draw the structures of the following compounds. a....Ch. 3.3B - Without looking at the structures, give molecular...Ch. 3.4C - Prob. 3.10P
Ch. 3.7B - Prob. 3.11PCh. 3.7C - Draw a graph similar to Figure 3-9, of the...Ch. 3.8B - Draw a graph similar to Figure 3-11, of the...Ch. 3.9 - Draw a perspective representation of the most...Ch. 3.10C - Give IUPAC names for the following compounds.Ch. 3.10C - Draw the structure and give the molecular formula...Ch. 3.11 - Which of the following cycloalkanes are capable of...Ch. 3.11 - Give IUPAC names for the following cycloalkanes.Ch. 3.12B - The heat of combustion of...Ch. 3.12C - Prob. 3.20PCh. 3.13B - The cyclohexane chair shown in Figure 3-22 has the...Ch. 3.13B - Draw 1,2,3,4,5,6-hexamethylcyclohexane with all...Ch. 3.14 - Prob. 3.23PCh. 3.14 - Prob. 3.24PCh. 3.14 - Draw the most stable conformation of a....Ch. 3.15 - Prob. 3.26PCh. 3.15 - a. Draw both chair conformations of cis-1...Ch. 3.15 - Prob. 3.28PCh. 3.15A - Draw the two chair conformations of each of the...Ch. 3.15B - Draw the most stable conformation of a....Ch. 3.16A - Name the following compounds.Ch. 3.16B - Prob. 3.32PCh. 3 - Prob. 3.33SPCh. 3 - Prob. 3.34SPCh. 3 - 3-35 a. Draw and name the five cycloalkane...Ch. 3 - Draw the structure that corresponds with each...Ch. 3 - Each of the following descriptions applies to more...Ch. 3 - Write structures for a homologous series of...Ch. 3 - Prob. 3.39SPCh. 3 - Construct a graph, similar to Figure 3-11, of the...Ch. 3 - The following names are all incorrect or...Ch. 3 - In each pair of compounds, which compound has the...Ch. 3 - There are eight different five-carbon alkyl...Ch. 3 - Use a Newman projection about the indicated bond...Ch. 3 - a. Draw the two chair conformations of...Ch. 3 - Draw the two chair conformations of each compound,...Ch. 3 - Using what you know about the conformational...Ch. 3 - Prob. 3.48SPCh. 3 - Draw Newman projections along the C3C4 bond to...Ch. 3 - Prob. 3.50SPCh. 3 - The most stable form of the common sugar glucose...Ch. 3 - This is a Newman projection of a substituted...
Knowledge Booster
Similar questions
- (a) (d) 5. Assign the R and S configurations for all stereogenic centers in the following compounds. BI H CH(CH₂)₂ KAMION WOH H₂C H CH₂ Br -H Br +H CH, (0) CH=CH₂ H+C₂0 -C=CCH₂ CH₂CH₂CH₂C1 CH₂CH₂CI H₂NH CH₂CH₂Cl CH₂CH₂CH₂OH H₂N CH₂CH₂OH CH₂arrow_forwardFor each organic compound in the table below, enter the locant of the highlighted side chain. compound CH 3 | CH₂ - CH - CH₂ - C - CH₂ 1 1 CH3 - CH₂ I CH3 CH3 CH₂ CH3 t CH₂-C- CH₂ - CH - CH₂ CH3 CH3 1 CH3 CH₂-C- | CH3 CH3 locant of highlighted side chain 0 3arrow_forwardWhat are the relative energy levels of the three staggered conformations of 2,3-dimethylbutane when looking down the C2-C3 bond? Me Me H Me Me Me Me Me. Me Conformation: 191 1ක් පුදා H Me Me Me H H H A B C Me A is the highest energy conformation and C is the lowest (energy level of B is in between the two) O A and B are equal energy, and C is the highest energy conformation A and B are equal energy, and C is the lowest energy conformation C is the highest energy conformation and A is the lowest (energy level of B is in between the two) O B is the highest energy conformation and C is the lowest (energy level of A is in between the two)arrow_forward
- Predict the relative pKa values of cyclopropene and cyclopropane.arrow_forwardA 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.arrow_forwardWhich of these products is the result of a hydride shift occuring during the substitution reaction of aqueous 2-chloro-3-methylpentane? CH3CH2CCH2CH3 || CH2 CH3CH(OH)CH(CH3)CH2CH3 CH2=CHC(CH3)=CHCH3 CH3CH=C(CH3)CH2CH3 CH3CH2C(CH3)CH2CH3 | OHarrow_forward
- Build a model of each of the four stereoisomers of 2,3-dibromopentane. Why does 2,3-dibromopentane have four stereoisomers, whereas 2,3-dibromobutane has only three?arrow_forwardEsc smooth 0 CH₂- Ph -CH-CH3 (3) (CH3)3C-C=C—CH(CH3)CH₂CH3 CH3 5c CH₂-C=C-C-OH T CH₂CH3 CH3 C C-CH₂CH3 53-methyloct-4-yne H₂C CH3 H C=C-CH₂CH₂ CH3 -CBr₂ C=C-CH3 CH,–C=C–CH3 Ph-C=C-H (CH₂)₂C-C=C—CH(CH₂) CH₂CH3 Chapter 9 Alkynes Quiz 2 1. Name each molecule. 2. Use the molecules in the reactions 1 through 9 highlighted in red to determine the product. 3. Draw the line/angle or skeletal structure of eachmolecule. 4. Use the alkyne below to predict the products 1- 9.arrow_forwardFollowing is a staggered conformation for one of the enantiomers of 2-bromobutane, and several purported Newman projections for this conformation. H H H3C Br H CH3 2-bromobutane H H (a) Is this (R)-2-bromobutane or (S)-2-bromobutane? CH3 CH3 Br H H H CH3 Br b CH3 H Br H CH3 CH3 H (b) Which of the following Newman projections is equivalent to the wedge-dash structure when viewed along the horizontal axis?arrow_forward
- Name the following compound: Br O (1S, 3S,4R)-1-chloro-3-bromo-4-isopropylcyclohexane O (1R, 2R, 5R)-1-bromo-2-isopropyl-5-chlorocyclohexane O (1R, 2S, 4R)-2-bromo-4-chloro-1-isopropylcyclohexane O (1S, 25, 4R)-2-bromo-4-chloro-1-isopropylcyclohexane O (15, 25, 5R)-1-bromo-2-isopropyl-5-chlorocyclohexanearrow_forward4 – Use bond-dissociation enthalpies (pg 167 of text) to calculate the DHo for each of the following reactions. CH3CH2CH3 + H2 g CH3CH3 + CH4 CH3CH2Cl + HI g CH3CH2I + HClarrow_forward2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning