EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3.11, Problem 42P
Using Newman projections, draw the most stable conformer for each of the following:
- a. 3-methylpentane, viewed along the C-2—C-3 bond
- b. 3-methylhexane, viewed along the C-3—C-4 bond
- c. 3,3-dimethylhexane, viewed along theC-3—C-4 bond
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Chapter 3 Solutions
EBK 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. 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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- Using Newman projections and an energy diagram, draw all of the conformers of 1,1,2- tribromoethane and indicate the energy changes that arise from rotation about the C-C bond. You do not need the actual energy values, but you should label relative energies (energy minima and maxima).arrow_forwardWhich of the following statements regarding cycloalkanes is wrong? a. The least strained form of any unsubstituted cycloalkane is the boat conformation of cyclohexane b. The planar form of any cycloalkane with a ring larger than cyclopropane will not be the most stable conformation c. Cyclopentane is nonplanar to avoid the torsional strain between adjacent C-H bonds. d. A di-substituted cycloalkane can have cis-trans isomers.arrow_forward10 draw the condensed and line bond structure of the compoundarrow_forward
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- Write the Condensed formula of the following: 1. 2,5-dibromo-3,3-dimethyl-4-propyloctane 2. trans-1-bromo-3-cholorocyclopentane 3. 4-cholorocyclopent-1-enearrow_forwardDraw the two chair conformations for each of the following compounds and indicate which conformer is more stable.arrow_forward2. The molecules shown below are four terpineol isomers. They are isolated from plants and have distinct aromas. For example, a -terpineol is a common perfume ingredient and smells similar to lilacs. HO a-terpineol ß-terpineol y-terpineol 4-terpineol A) How many of each of the different types of carbon are present in 4-terpineol. Do not consider carbons attached to heteroatoms or participating in pi bonds. i. Primary ii. Secondary iii. Tertiary iv. Quaternary B) Terpineols contain tertiary alcohols. While quaternary carbons exist, quaternary alcohols do not. Explain why a quaternary alcohol is not feasible. C) Is it necessary to use E/Z designations for any of these molecules? If so, provide the proper designation for each relevant molecule. If not, briefly explain why it isn't needed. e. Draw a structural isomer of terpineol that meet the following criteria. You should draw one unique structure for each set. You must draw each molecule twice, once as a skeletal structure and once as a…arrow_forward
- Draw the most stable conformer of the following compounds, using Newman projections.arrow_forward9. Using Newman projections, draw the most stable conformer for the following: 3-methylpentane, considering rotation about the C-2-C-3 bond b. 3-methylhexane, considering rotation about the C-3-C-4 bond 3,3-dimethylhexane, considering rotation about the C-3-C-4 bond lavalahavane, a. C.arrow_forwardUsing Newman projections, draw the most stable conformer for each of the following: a. 3-methylpentane, viewed along the C@2-C@3 bondb. 3-methylhexane, viewed along the C@3-C@4 bondc. 3,3-dimethylhexane, viewed along the C@3-C@4 bondarrow_forward
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