Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 3, Problem 36P
Interpretation Introduction
Interpretation:
An approximate potential energy diagramis to be sketched for rotation about the carbon-carbon bond in
Concept introduction:
The potential energy diagram shows the variation in the energy of the conformations for the different torsion angles for the rotation about the carbon-carbon bond.
When the torsion angle is approximately
When the torsion angle is approximately
When the torsion angle is approximately
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Here is the chemical structure of 2-bromobutane:
H
H.
H
C-C-H
H :Br: H H
Decide whether each molecule in the table below is another molecule of 2-bromobutane, a molecule of an isomer of 2-bromobutane, or a molecule of an entirely
different compound.
molecule
relationship to 2-bromobutane
CH,
(Choose one)
H,c=ċ=CH,-Br
Explanation
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Square planar molecules with formula AB2C2 and octahedral molecules with formulas AB4C2 and AB3C3 feature diastereoisomers. Recall that trigonal bipyramidal geometry features two distinct positions: axial and equatorial. Draw all diastereoisomers for trigonal bipyramidal molecules with formula (a) AB4C and (b) AB3C2. You must indicate the stereochemistry using full and dashed wedges and label all positions as either axial (ax) and equatorial (eq)..
The unsaturation number or degree of unsaturation (U) can be used to determine the number of rings and multiple bonds in a compound from its molecular formula. Given a structure, you can determine the number of hydrogens without having to count them explicitly. Consider three compounds and their degree of unsaturation.
(a) A compound A has the molecular formula C7H13ClN2OC7H13ClN2O. How many rings and/or π bonds does it contain?
Chapter 3 Solutions
Organic Chemistry - Standalone book
Ch. 3.1 - Identify the alkanes corresponding to each of the...Ch. 3.1 - Find the conformations in Figure 3.4 in which the...Ch. 3.2 - Sketch a potential energy diagram for rotation...Ch. 3.2 - Acetylcholine is a neurotransmitter in the central...Ch. 3.2 - Prob. 5PCh. 3.5 - The heats of combustion of ethylcyclopropane and...Ch. 3.8 - Prob. 7PCh. 3.10 - The following questions relate to a cyclohexane...Ch. 3.10 - Draw the most stable conformation of...Ch. 3.11 - Prob. 10P
Ch. 3.11 - Prob. 11PCh. 3.12 - Based on what you know about disubstituted...Ch. 3.12 - Write structural formulas for the most stable...Ch. 3.14 - Cubane (C4H8) is the common name of the polycyclic...Ch. 3.14 - Prob. 15PCh. 3.14 - Prob. 16PCh. 3.14 - Prob. 17PCh. 3.14 - Prob. 18PCh. 3.15 - Prob. 19PCh. 3 - Give the IUPAC names of each of the following: (a)...Ch. 3 - Draw Newman projections for the gauche and...Ch. 3 - Identify all atoms that are (a) anti and (b)...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Prob. 25PCh. 3 - Prob. 26PCh. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Oxidation of 4-tert-butylthiane proceeds according...Ch. 3 - The following are representations of two forms of...Ch. 3 - Draw (a) a Newman projection of the most stable...Ch. 3 - Write a structural formula for the most stable...Ch. 3 - Sight down the C-2-C-3 bond, and draw Newman...Ch. 3 - Prob. 34PCh. 3 - Sketch an approximate potential energy diagram for...Ch. 3 - Prob. 36PCh. 3 - Even though the methyl group occupies an...Ch. 3 - Which do you expect to be the more stable...Ch. 3 - Arrange the trimethylcyclohexane isomers shown in...Ch. 3 - Identify the more stable stereoisomer in each of...Ch. 3 - One stereoisomer of 1,1,3,5-tetramethylcyclohexane...Ch. 3 - One of the following two stereoisomers is...Ch. 3 - In each of the following groups of compounds,...Ch. 3 - The heats of combustion of the more and less...Ch. 3 - The measured dipole moment of ClCH2CH2Cl is 1.12D....Ch. 3 - Prob. 46PCh. 3 - Prob. 47PCh. 3 - Prob. 48DSPCh. 3 - Prob. 49DSPCh. 3 - Prob. 50DSPCh. 3 - Prob. 51DSPCh. 3 - Prob. 52DSPCh. 3 - Prob. 53DSP
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- 4. Read section 3.10. Draw a bond-line structure of the most stable conformation for methylcyclohexane, with the methyl in an equatorial position (be sure to draw that equatorial position in its correct location!!)arrow_forwardIs the geometry of CH2BrCl, the same as CH3Cl and CH4? Briefly explain the evidence for your answerarrow_forwardMolecules that have the same molecular formula, but different atomic connections are called constitutional isomers. Draw and name the five constitutional isomers of C6H14. Is this correct answer from this paper that I draw for the name the five constitutional isomers of C6H14? Can you explain to me that why is the different atomic connections are called constitutional isomers?arrow_forward
- An electrostatic potential map of calicene is shown below. a) Both the electrostatic potential map and its significant dipole moment indicate that calicene is an unusually polar hydrocarbon. Which of the dipolar resonance forms, structure A or structure B, better corresponds to the electron distribution in the molecule? Select the single best answer. b) Which one of the following structures should be stabilized by resonance to a greater extent? Select the single best answer.arrow_forwardRank the following substituents in increasing bulkiness (size), from smallest (top) to largest (bottom). tert- butyl group ethyl group fluorine atom hydrogen atom Rank the following substituents in increasing bulkiness (size), from smallest (top) to largest (bottom). Drag and drop options into correct order and submit. For keyboard navigation... SHOW MORE ✓ III = ||| ||| = = ||| tert-butyl group ethyl group fluorine atom hydrogen atomarrow_forwardDetermine the total number of σ bonds and the total number of π bonds in levomenol (Problem 3.34).arrow_forward
- 4. One of the resonance structures of "tropylium ion" (C7H7*) is shown below. It is planar and aromatic with Hückel number of p-n electrons where n=1. Draw all the other contributing resonance structures. (There are more than two.) Based on the “average" of the contributing resonance structures, how close does the average ring carbon get to its "octeť" in tropylium ion?arrow_forwardPart G. Molecules with Oxygen and Nitrogen. Organic molecules often contain the elements oxygen and nitrogen. Construct a model with the molecular formula C5H12O where the oxygen is bonded to one hydrogen. When a hydrogen is bonded to an oxygen or nitrogen, you need to draw that bond in a bond-line structure. Draw the bond-line structure of this model. What is the molecular geometry of oxygen in your structure? Draw three more constitutional isomers with the molecular formula C5H12O where the oxygen is bonded to one hydrogen. Structure Structure Structure Draw three more constitutional isomers with the molecular formula C5H12O where the oxygen is bonded to two carbon atoms. Structure Structure Structurearrow_forwardOctane has several isomers. Which of the following condensed formulas is NOT an isomer of octane? (You may select more than one. Incorrect answers will be penalised.) (C3H7)2CCH3 (C₂H5)2CHCH(CH3)2 (C₂H5)2CHC3H7 (C2H5)3CHCH3arrow_forward
- Does cyclooctene have two distinct configurations about its C=C bond? Hint: Consider using a model kit. Cyclooctenearrow_forwarda) Draw all Newman projections of your molecule's conformations in which the CH3 group and the H of the CHY2 group are positioned 'ANTI' to each other. Be sure to put in the correct X and Y atoms, bonded to the correct C atoms, for your molecule. X = FY=I Conformations = 60 deg and - 180 deg 60 deg dihedral angle = - 179.987 deg 180 deg · - dihedral angle = 179.814 degarrow_forwardConsider each pair of structures below. Indicate the isomeric relationship between each pair. Your choices are (i) identical structures (ii) constitutional isomers, (iii) conformational isomers, (iv) configurational isomers or (v) resonance structures.arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License