Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 4.2, Problem 6P
Prostaglandin F2α, a hormone that causes uterine contraction during childbirth, has the following structure. Are the two hydroxyl groups (-OH) on the cyclopentane ring cis or trans to each other? What about the two carbon chains attached to the ring?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Linoleic acid is an essential fatty acid found in many vegetable oils, such as soy, peanut, and cottonseed. A key structural feature of the molecule is the cis orientation around its two double bonds, where R1 and R2 represent two different groups that form the rest of the molecule.
(a) How many different compounds are possible, changing only the cis-trans arrangements around these two double bonds?
(b) How many are possible for a similar compound with three double bonds?
Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died.
Q.) Write a Lewis structure for methyl isocyanate and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom?
If you rotate the hydrogen atoms to a different position in a a model of C2H6 by turning about the central C—C bond, do you get different structural (or constitutional) isomers of C2H5Cl?
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
Knowledge Booster
Learn more about
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
- Select the bonds in the 3D representation of methyl urethane below that are multiple bonds. (Hint: Consider the number of bonds attached to an atom in the image compared to the normal valence of that atom. In a valid structure, the number of bonds to an atom will equal the valence of that atom.) • Gray = C: white = H; red = 0; blue = N; dark green = Cl; brown = Br; light green = F; purple = 1; yellow = S: orange = P. • Double click to select bonds. You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens). ●arrow_forwardOne way of naming alcohols is to name the alkyl group that is attached to the −OH and add the word alcohol. Write bond-line formulas for (a.) propyl alcohol and (b.) isopropyl alcohol.arrow_forwardThe average bond energy (enthalpy) for a C=CC=C double bond is 614 kJ/molkJ/mol and that of a C−CC−C single bond is 348 kJ/molkJ/mol. Estimate the energy needed to break only the ππ bond of the double bond of 2-butene. Express your answer numerically in joules per molecule.arrow_forward
- five examples of structures with this formula (C6H12). At least one should containa ring, and at least one should contain a double bondarrow_forwardTwo or more of your answers are incorrect. Use this condensed chemical structure to complete the table below. O || CH,=CH–C-H The condensed chemical structure of acrolein Some facts about the acrolein molecule: number of carbon-carbon single (CC) bonds: number of carbon-hydrogen single (CH) bonds: number of lone pairs: X S 2 1 4arrow_forwardLinoleic acid (below) is an essential fatty acid found in many vegetable oils, such as soy, peanut, and cottonseed. A key structural feature of the molecule is the cis orientation around its two double bonds, where R1 and R2 represent two different groups that form the rest of the molecule. R, CH2 `H H' (a) How many different compounds are possible, changing only the cis/trans arrangements around these two double bonds? (b) How many are possible for a similar compound with three double bonds? R3. .CH2 R4 `H H `H H'arrow_forward
- We have thus far determined the single bond connectivity for (CH, ),CO as: H Н—с—с-—с—н H H There are six valence electrons still unaccounted. Carbon must form four bonds in order to satisfy the octet rule. Add a bond to carbon and fill in the remaining missing electrons. Select Draw Rings More H H. H H Harrow_forwardWhich of the following compounds show cis-trans isomerism? Draw the cis and trans isomers of those that do.arrow_forwardIdentify the functional group/s of the following organic compounds `N ОН Соcaine A°-Tetrahydrocannabinol (THC) Lysergide (lysergic acid diethyl amide, or LSD) `NH НО. HN + H3N ОН Aspartame (NutraSweet) Theobromine Caffeine Azidothymidine (AZT) ОН F3C. 'N H2 Penicillin G НО Propofol Fluoxetine hydrochloride (Prozac) HO Na+ Dextromethamphetamine Naproxen sodium (Aleve) Acetylsalicylic acid (Aspirin)arrow_forward
- What are the functional groups of Carvone? Identify and label all functional groups (alcohols, amines, amides, carboxylic acids, ketones, aldehydes, aromatic rings, aromatic amines, etc) on the Lewis Structure. You do not have to circle alkanes.arrow_forward||| O NAMING AND DRAWING ORGANIC MOLECULES Interpreting condensed chemical structures Use this condensed chemical structure to complete the table below. 0 NH₂ - CH — C — OH | CH3 The condensed chemical structure of alanine Some facts about the alanine molecule: number of carbon-carbon single (C - C) bonds: number of carbon-hydrogen single (C-H) bonds: number of oxygen-hydrogen single (O - H) bonds: number of nitrogen-hydrogen single (N - H) bonds: number of lone pairs: X Ś 0 ☐ 1 D 503 Jessarrow_forwardHydrogen cyanide can be catalytically reduced with hydro-gen to form methylamine. Use Lewis structures and bond ener-gies to determine ΔH°ᵣₓₙ for HCN(g)+2H₂(g)→CH₃NH₂(g)arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage LearningChemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Lipids - Fatty Acids, Triglycerides, Phospholipids, Terpenes, Waxes, Eicosanoids; Author: The Organic Chemistry Tutor;https://www.youtube.com/watch?v=7dmoH5dAvpY;License: Standard YouTube License, CC-BY