Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 4.SE, Problem 25VC
The following cyclohexane derivative has three substituents-red, green, and blue. Identify each substituent as axial or equatorial, and identify each pair of relationships (red-blue, red-green, and blue- green) as cis or trans.
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Q2 Give the stereochemical relationships between each pair of structures. Examples are
same compound, structural isomers, enantiomers, diastereomers.
(a)
CH,
CH,
CHOH
CHOH
CH,
CH,
H OH HO-H
H OH HO H
H--CH HO-
HO H
H-
OH HO-
OH HO H
H-OH
CH,
CH,
CH,
CH,
CH,
CH,
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.) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet
(a) Draw all stereoisomers formed by monobromination of the cis and trans isomers of 1,2-dimethylcyclohexane drawn
below. (b) How do the products formed from each reactant compare-identical compounds, stereoisomers, or
constitutional isomers?
cis-1,2-dimethylcyclohexane
trans-(1R.2S)-dimethylcyclohexane
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...
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- A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.arrow_forwardLook at the diagram below and then please answer the following questions: 1) What is the name of the least stable conformation associated with the 6-atom ring? 2) Illustrate a chair-chair interconversion equilibrium for the compound. Show all ring substituents (including H atoms), and give axial or equatorial labels only for the non-H substituents. Which side of your equilibrium is favored and why? (CH2)3CH3 OH 6, N. HOH2C 4 Ноarrow_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
- 3. Rank the substituents in each of the following sets: (а) -Н, -ОН, -СH2CH3, -СH2CH2ОН (b) -СО2Н, -СО2CH3, -СH2ОН, -он (c) –CN, –CH2NH2, -CH2NHCH3, –NH2 (d) –SH, -CH2SCH3, –CH3, -SSCH3arrow_forwardAssume that you have a variety of cyclohexanes substituted in the positions indicated. Identify the substituents as either axial or equatorial. For example, a 1,2-cis relationship means that one substituent must be axial and one equatorial, whereas a 1,2-trans relationship means that either both substituents are axial or both are equatorial. a) 1,6-cis-disubstituted b) 1,2-trans-disubstituted c) 1,3-trans-disubstitutedarrow_forwardWhen (1-bromoethyl)cyclopentane is heated in water for an extended period of time, SIX products result: three alcohols and three alkenes. Draw the three alcoholsarrow_forward
- cOH CH2OH H, ОН Н Ha ÓH H In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: equatorial Group b: axial Group c: equatorialarrow_forwardAssume that you have a variety of cyclohexanes substituted in the positions indicated. Identify the substituents as either axial or equatorial. For example, a 1,2-cis relationship means that one substituent must be axial and one equatorial, whereas a 1,2-trans relationship means that either both substituents are axial or both are equatorial. a) 1,4-cis-disubstituted b) 1,6-cis-disubstituted c) 1,2-cis-disubstituted Submit Answer Try Another Version 6 item attempts remaining optioins fill please both axial only both equatorial only both axial or both equatorial one axial-one equatorialarrow_forwardDraw both cis- and trans-1,4-dimethylcyclohexane in their more stable chairconformations. (a) How many stereoisomers are there of cis-1,4-dimethylcyclohexane, and how many of trans-1,4-dimethylcyclohexane? (b) Are any of the structures chiral? (c) What are the stereochemical relationships among the various stereoisomers of 1,4-dimethylcyclohexane?arrow_forward
- Assume that you have a variety of cyclohexanes substituted in the positions indicated. Identify the substituents as either axial or equatorial.For example, a 1,2-cis relationship means that one substituent must be axial and one equatorial, whereas a 1,2-trans relationship means that either both substituents are axial or both are equatorial. a) 1,3-cis-disubstituted b) 1,2-trans-disubstituted c) 1,4-trans-disubstitutedarrow_forwardDraw and name the six isomeric cyclopentane of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.arrow_forward7.33 a-Farnesene is a constituent of the natural wax found on apples. What is its IUPAC name, including stereochemistry? 7.34 Menthene, a hydrocarbon found in mint plants, has the systematic name 1-isopropyl-4-methylcyclohexene. Draw its structure. 7.35 Draw and name the six alkene isomers, C5H1o, including E,Z isomers. a-Famesene 8.22 Name the following alkenes, and predict the products of their reaction with (1) meta-chloroperoxybenzoic acid, (2) KMnO4 in aqueous acid, and (3) 03, followed by Zn in acetic acid: (a) (b) (a) 8.23 Draw the structures of alkenes that would yield the following alcohols on hydration (red = O). Tell in each case whether you would use hydroboration- oxidation or oxymercuration-demercuration. (b)arrow_forward
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