Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3, Problem 86P
Bromine is a larger atom than chlorine, but the equilibrium constants in Table 3.9 indicate that a chloro substituent bus a greater preference for the equatorial position than does a bromo substituent. Suggest an explanation for this fact.
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An electrostatic potential map of calicene is shown below.
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b) Which one of the following structures should be stabilized by resonance to a greater extent? Select the single best answer.
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An alkyne with molecular formula C5H10
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A saturated hydrocarbon with molecular formula C6H14
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Hydrocarbon A possesses a significant dipole, even though it is composed of only C—C and C—H bonds. Explain why the dipole arises and use resonance structures to illustrate the direction of the dipole. Which ring is more electron rich?
Chapter 3 Solutions
Organic Chemistry (8th Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structure of a compound with molecular...Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Prob. 6PCh. 3.1 - Draw the structure for each of the following: a....Ch. 3.1 - Name the following compounds: a. CH3OCH2CH3 b....Ch. 3.2 - Prob. 9PCh. 3.2 - Draw the structure for each of the following: a....Ch. 3.2 - Give each substituent on the nine-carbon chain a...Ch. 3.2 - Prob. 14P
Ch. 3.3 - What is each compounds systematic name?Ch. 3.3 - Prob. 16PCh. 3.3 - Prob. 17PCh. 3.3 - Prob. 18PCh. 3.3 - Prob. 19PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 21PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Prob. 25PCh. 3.6 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Draw condensed and skeletal structures for each of...Ch. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 32PCh. 3.9 - Prob. 33PCh. 3.9 - Prob. 34PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.10 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - Prob. 38PCh. 3.10 - Prob. 39PCh. 3.11 - a. Draw all the staggered and eclipsed conformers...Ch. 3.11 - Prob. 41PCh. 3.11 - Using Newman projections, draw the most stable...Ch. 3.12 - The bond angles in a regular polygon with n sides...Ch. 3.12 - Prob. 44PCh. 3.13 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.14 - Using the data in Table 3.9, calculate the...Ch. 3.14 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.15 - Prob. 48PCh. 3.15 - Which has a higher percentage of the...Ch. 3.15 - a. Draw the more stable chair conformer of...Ch. 3.15 - For each of the following disubstituted...Ch. 3.15 - a. Draw Newman projections of the two conformers...Ch. 3.15 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 56PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 66PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 69PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 72PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - What is each compound s systematic name?Ch. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 88PCh. 3 - Using the data obtained in Problem 85, calculate...Ch. 3 - Draw the conformers for the following...
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- Choose the correct answer. Choose... Choose.. An aldehyde with molecular formula C2H6O A ketone with molecular formula C3H60 A ketone with molecular formula C2H60 An alkene with molecular formula C5H10 An alcohol with molecular formula C4H8O A saturated hydrocarbon with molecular formula C6H14 An unsaturated hydrocarbon with molecular formula C6H12 An alkane with molecular formula C5H12 Choose...arrow_forwardRedraw compound 2.1 and label each carbon atom and the oxygen atom with its hybridisationarrow_forwardHere 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 Check O 2021 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Center I Accessibility P Type here to search 76°F DELL F1 F2 F3 F4 F5 FB F9 F10 F11 F12 PrtScr PAA @ %23 2$ 1 8. 9 Q W R Y. A F G H. K V N4 Alt Ctri Alt Σ B. C1arrow_forward
- Estimate the heat released when 1-butene(CH3CH2CHCH2) reacts with bromine to give CH3CH2CHBrCH2Br. Bond enthalpies are CH : 412 kJ/mol; CC : 348 kJ/mol;CC : 612 kJ/mol; CBr : 276 kJ/mol;BrBr : 193 kJ/mol. 1.317 kJ/mol 2.507 kJ/mol 3.95 kJ/mol 4.288 kJ/mol 5.181 kJ/molarrow_forwardChoose the correct answer. Choose.. Choose.. A saturated hydrocarbon with molecular formula C6H14 An alkyne with molecular formula C5H10 A ketone with molecular formula C4H80 An alkene with molecular formula C5H10 An aldehyde with molecular formula CH4O An alkene with molecular formula C5H8 A ketone with molecular formula C3H8O An aldehyde with molecular formula C2H4O Choose..arrow_forwardFluorene is essentially non-polar. Briefly explain, with respect to atoms that are present and absent in fluorene, and their relative electronegativities, why fluorene is non-polar.arrow_forward
- Examine the relative bond length and bond strength of the C–C and C–Hbonds in ethane, ethylene, and acetylene ?arrow_forwardWrite the systematic name of each organic molecule: structure CH3 - CH₂ - CH₂ - CH₂ - -O–CH2 CH3 CH3- O−C−CH2−CH2–CH2–CH3 CH3 O O || C- - CH₂ - CH3 name 0arrow_forwardHydrocarbon A possesses a significant dipole, even though it iscomposed of only C—C and C—H bonds. Explain why the dipole arisesand use resonance structures to illustrate the direction of the dipole.Which ring is more electron rich?arrow_forward
- Specify whether the two structures are resonance contributors to the same resonance hybrid. Be sure to explain your reasoning. If yes, be sure to specify which is preferred and why. H2C=NH2arrow_forwardThe 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?arrow_forwardProvide a complete, labeled orbital diagram for 1-fluoro-butadiene (FHC=CH-CH=CH2). Indicate all bond types (including which orbitals have overlapped to form each bond) and bond angles.arrow_forward
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