Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 4, Problem 4.70P
Haloethanes
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Haloethanes (CH3CH2X, X = Cl, Br, I) have similar barriers to rotation (13.4–15.5 kJ/mol) despite the fact that the size of the halogen increases, Cl ? Br ? I. Offer an explanation.
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Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- 2NaOH(a)+CaCl2(s)+2NaCl(s)arrow_forwardFor example, alanine is a chiral amino acid that has two enantiomers: (+)-alanine and (-)-alanine. These two are optical isomers. NH2 NH2 4. One of the most important properties of chiral molecules in solution is their effect on plane- polarized light, this effect is called optical activity. -C H 2 COOH HOOC CH When an enantiomer rotates a plane-polarized light in the positive direction or clockwise, it is dextrorotary (+ or d), while for a negative direction or counterclockwise, it is levorotary (- or l) (+)-Alanine (-)-Alanine Alanine is a chiral amino acid that has two enantiomers: (+)-alanine and ()-alanine. These two are optical isomers.arrow_forward11. Which statement is true of the carbon-carbon bonds in benzene? (a) They are identical to the carbon-carbon bonds in cyclohexane. (b) They are identical to the carbon-carbon bonds in cyclohexene. (c) They are half-way between a double and single bond. (d) They are easily broken in chemical reactions. (e) They are all double bonds. ct Copyright O 2002 McGraw-Hill Ryerson Limited Name: Class:arrow_forward
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- Your 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_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 the following questions. What is the geometry and hybridization of the carbon in CH4? What is the geometry and hybridization of each central carbon atom in the remaining molecules? Draw each molecule showing the bonds and identify each bond in all the molecules as s or p. 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_forwardArrange the following alkyl halides in order of increasing boiling point:(CH 3)3Br, (CH 3)2CH C(CH3) 2Br, (CH 3) 2CHBr, CH 3CH 2F.arrow_forward
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