Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 3, Problem 83P
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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Bromine is a larger atom than chlorine, but the equilibrium constants in Table 3.9 indicate that a chloro substituent has a greater preference for the equatorial position than does a bromo substituent. Suggest an explanation for this fact.
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Chapter 3 Solutions
Organic Chemistry
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. 11PCh. 3.2 - Prob. 12PCh. 3.3 - Prob. 13PCh. 3.3 - Prob. 14P
Ch. 3.3 - Prob. 15PCh. 3.3 - Prob. 16PCh. 3.3 - What is each compounds systematic name?Ch. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 19PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Prob. 23PCh. 3.6 - Prob. 24PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Prob. 26PCh. 3.7 - Prob. 27PCh. 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. 30PCh. 3.9 - Prob. 31PCh. 3.9 - Prob. 32PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.9 - Prob. 35PCh. 3.9 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - a. Draw all the staggered and eclipsed conformers...Ch. 3.10 - Prob. 38PCh. 3.10 - Using Newman projections, draw the most stable...Ch. 3.11 - The bond angles in a regular polygon with n sides...Ch. 3.11 - Prob. 41PCh. 3.11 - Prob. 42PCh. 3.12 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.13 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.13 - Using the data in Table 3.9, calculate the...Ch. 3.14 - Prob. 46PCh. 3.14 - Which has a higher percentage of the...Ch. 3.14 - For each of the following disubstituted...Ch. 3.14 - 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. 53PCh. 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. 63PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 66PCh. 3 - Prob. 67PCh. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 69PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Prob. 71PCh. 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 - Prob. 80PCh. 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. 85PCh. 3 - Using the data obtained in Problem 85, calculate...
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- Redraw compound 2.1 and label each carbon atom and the oxygen atom with its hybridisationarrow_forwardChoose 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_forwardHydrocarbon 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?arrow_forward
- 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 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_forwardEstimate 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_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_forwardSpecify 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_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_forward
- 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?arrow_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_forwardYour chemistry professor draws a number of molecules on the board: (1) CH4 ; (2) H2C=CH2 ; (3) H2C=C=CH2 ; and (4) H2C=C=C=CH2. You muse about all the molecules that chemists draw on a two-dimensional board and wonder which ones are actually planar, existing basically as they appear on the board, and which ones are not plane but rather three-dimensional. Answer ALL of the following questions. What are the specific orbital overlaps (i.e., sp3-sp3) that are in each of the molecules? What are the bond angles for each central atom in each molecule? Which molecules are planar and which are non-planar?arrow_forward
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