Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 7.3B, Problem 7.4P
For each of the following molecular formulas, determine the number of elements of unsaturation, and draw three examples.
- a. C4H4Cl2
- b. C4H8O
- c. C6H8O2
- d. C5H5NO2
- e. C6H3NClBr
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QUESTION 9
Draw the lowest energy conformer of each of the 5 compounds
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Consider pentane, C5H12. Looking through the internal C3-C4single bond, draw thesix Newman projections (where the angle between two bonds as you look through the C3and C4bond is either 0°or 60°of the different conformations. Label the conformers/rotamers using I, II, etc.
a.Which conformer is the most stable? the least stable?
b.Which rotamer is the anticonformer? the gaucheconformer?
c.Draw the anticonformer in saw horse projection.
Chapter 7 Solutions
Organic Chemistry (9th Edition)
Ch. 7.3A - Prob. 7.1PCh. 7.3A - Prob. 7.2PCh. 7.3B - Draw five more compounds of formula C4H6NOC1.Ch. 7.3B - For each of the following molecular formulas,...Ch. 7.4 - Give the systematic (IUPAC) names of the following...Ch. 7.5B - The following names are all incorrect. Draw the...Ch. 7.5B - Prob. 7.8PCh. 7.5B - a. How many stereogcmc double bonds are in...Ch. 7.6 - Teflon-coated frying pans routinely endure...Ch. 7.7B - Prob. 7.11P
Ch. 7.8B - Use the data in Table7-2 to predict the energy...Ch. 7.8C - Prob. 7.13PCh. 7.8E - Explain why each of the following alkenes is...Ch. 7.8F - Prob. 7.15PCh. 7.10 - Prob. 7.16PCh. 7.10A - SN1 substitution and E1 elimination frequently...Ch. 7.10C - Prob. 7.18PCh. 7.10C - Prob. 7.19PCh. 7.10C - Prob. 7.20PCh. 7.11 - Prob. 7.21PCh. 7.11 - Prob. 7.22PCh. 7.12 - Prob. 7.23PCh. 7.12 - Prob. 7.24PCh. 7.13 - Prob. 7.25PCh. 7.14B - Prob. 7.26PCh. 7.14B - Make models of the blowing compounds, and predict...Ch. 7.15 - Prob. 7.28PCh. 7.15 - Prob. 7.29PCh. 7.15 - Prob. 7.30PCh. 7.15 - Prob. 7.31PCh. 7.16 - Predict the major and minor elimination products...Ch. 7.17B - Predict the products and mechanisms of the...Ch. 7.18 - Propose mechanisms for the following reactions.Ch. 7.18 - Prob. 7.35PCh. 7.19B - The dehydrogenation of butane to trans-but-2-ene...Ch. 7.19B - Prob. 7.37PCh. 7.19B - Prob. 7.38PCh. 7.19B - Prob. 7.39PCh. 7 - Prob. 7.40SPCh. 7 - Prob. 7.41SPCh. 7 - Prob. 7.42SPCh. 7 - Prob. 7.43SPCh. 7 - Prob. 7.44SPCh. 7 - Prob. 7.45SPCh. 7 - Prob. 7.46SPCh. 7 - The energy difference between cis- and...Ch. 7 - Prob. 7.48SPCh. 7 - Prob. 7.49SPCh. 7 - Prob. 7.50SPCh. 7 - What halides would undergo E2 dehydrohalogenation...Ch. 7 - Prob. 7.52SPCh. 7 - Prob. 7.53SPCh. 7 - Write a balanced equation for each reaction,...Ch. 7 - Prob. 7.55SPCh. 7 - Using cyclohexane as your starting material, show...Ch. 7 - Show how you would prepare cyclopentene from each...Ch. 7 - Prob. 7.58SPCh. 7 - E1 eliminations of alkyl halides are rarely useful...Ch. 7 - Prob. 7.60SPCh. 7 - Propose mechanisms for the following reactions....Ch. 7 - Prob. 7.62SPCh. 7 - Prob. 7.63SPCh. 7 - Prob. 7.64SPCh. 7 - Prob. 7.65SPCh. 7 - Prob. 7.66SPCh. 7 - Prob. 7.67SPCh. 7 - Prob. 7.68SPCh. 7 - Prob. 7.69SPCh. 7 - Explain the dramatic difference in rotational...Ch. 7 - One of the following dichloronorbornanes undergoes...Ch. 7 - A graduate student wanted to make...Ch. 7 - Prob. 7.73SPCh. 7 - Prob. 7.74SPCh. 7 - Prob. 7.75SPCh. 7 - Prob. 7.76SP
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- What is the relationship between the following molecules? CH3 H. CH3 H. II H. H. H. H. H. H3C CH3 O Identicals Constitutional isomers O Resonance structures Conformational Isomersarrow_forwardAnalyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.arrow_forward15. Which C6H₁o isomer shown below is the least stable? A. IV C. III 11 B. II D. I IV brarrow_forward
- Which statement is true about these conformers? H. H. H H CH3 H3C H. H,C H,C H. H. A O A and B are equally stable O Difficult to predict O A more stable than B ) B more stable thanarrow_forwardChoose the statement that is incorrect about rings. اختر احدى الاجابات А. Planar cyclobutane is its most stable conformation. В. Planar cyclopentane would have small angle strain but severe torsional strain. C. The chair conformation of cyclohexane has no angle or torsional strain. D. Cyclopropane has the greatest angle strain. Е. The chair conformation has less torsional strain and fewer nonbonded interactions than the twist boat conformation.arrow_forwardXX. CH₂ H. H Label each pair of compounds below as: تے H₂C a. conformational isomers b. configurational isomers constitutional isomers identical not isomers C. d. e. CH3 CH 3 CH 3 and CI H CH3 and CH3 H H₂C- Н. H H H3C12 CH₂ CH3 CH3 CH₂ CI H3C- * The same letter can be use more than once!arrow_forward
- a) Draw the two ring flipped conformers of each molecule A and B. Indicate the more stable conformer, respectively. CH3 fCH3 H,C. CH3 H3C. CH3 CI CI A B a) Which is more stable between A and B? Why?arrow_forward4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane Iarrow_forwardCONH₂ CH3 CH3 H₂C=CHCHCH₂CO₂CH3 1. LiAlH4 2. H₂O 1. LiAlH4 2. H3O+arrow_forward
- For the following structural formula, pick the structure that accurately represents its MOST STABLE conformation. CH3 H₂Cl... Br Br Br H₂C O D. O B. O C. O A. CH3 A CH3 B CH3 ... Br 주 Br H3C C CH3 H3C CH3 Darrow_forwardWhat are 2 similarities between butane and isobutane in the most stable conformation? What are 2 differences?arrow_forwardA Newman projection of a disubstituted cyclohexane is shown below. Determine which of the following 2D representations matches the Newman projection. H Br H H2 CH3 `H H H2 Br II Br CH3 \CH3 Brill. Br Br IV H3 II CH3 Br Br Br A) I B) II C) II D) IVarrow_forward
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