Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 2, Problem 2.61P
Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum).
- (a) Complete the Lewis structure of each compound by showing all unshared electron pairs.
- (b) Predict bond angles about each carbon, oxygen, and nitrogen atom.
- (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
TRUE OR FALSE
(a) Both ethylene and acetylene are planar molecules.
(b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism.
(c) Cis-trans isomers have the same molecular formula but a different connectivity of their atoms.
(d) Cis-2-butene and trans -2-butene can be interconverted by rotation about the carbon–carbon double bond.
(e) Cis-trans isomerism is possible only among appropriately substituted alkenes.
(f) Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers.
(g) Cyclohexene can exist as a pair of cis-trans isomers.
(h) 1-Chloropropene can exist as a pair of cis-trans isomers.
Indicate whether each statement is true or false. (a) Twogeometric isomers of pentane are n-pentane and neopentane.(b) Alkenes can have cis and trans isomers around theCC double bond. (c) Alkynes can have cis and trans isomersaround the CC triple bond.
Ethanol (CH3CH2OH) and dimethyl ether (CH3OCH3) are constitutional isomers.
(a) Predict which of the two has the higher boiling point.
(b) Predict which of the two is more soluble in water.
Chapter 2 Solutions
Organic Chemistry
Ch. 2.2 - Do the line-angle formulas in each pair represent...Ch. 2.2 - Draw line-angle formulas for the three...Ch. 2.3 - Write IUPAC names for these alkanes.Ch. 2.4 - Combine the proper prefix, infix, and suffix and...Ch. 2.4 - Write the molecular formula, IUPAC name, and...Ch. 2.4 - Write molecular formulas for each bicycloalkane,...Ch. 2.4 - Prob. 2.7PCh. 2.5 - For 1,2-dichloroethane: (a) Draw Newman...Ch. 2.5 - Following is a chair conformation of cyclohexane...Ch. 2.5 - Draw the alternative chair conformation for the...
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw the structural formulas for the following compounds. Include all the bonds to hydrogen atoms. Be sure to answer both parts. (a) 1,4-dichloro-2-ethylbenzene: (b) 2-ethyl-1,3-dimethylbenzene:arrow_forwardTrue or false: (a) The C¬C bonds in benzene are all the samelength and correspond to typical single C¬C bond lengths.(b) The C¬C bond in acetylene, HCCH, is longer than theaverage C¬C bond length in benzene.arrow_forwardWrite structural formulas for compounds that meet the following descriptions:(a) An alkene, C6H12, that cannot have cis–trans isomersand whose longest chain is 5 carbons long(b) An alkene with a chemical formula of C10H12 that hascis–trans isomers and contains a benzene ring.arrow_forward
- (a) The compound given below had the following IUPAC name and structural formula dibromocyclopentane C3H6CHBrCHBr (i) What type of isomerism is possible in the organic compound? (ii) Draw all the pairs of possible isomers and name them.arrow_forward1. (a) Draw the structures of the eight isomeric pentyl alcohols, C3H11OH. (b) Name each by the IUPAC system and by the carbinol system. (c) Label each as primary, secondary, or tertiary, (d) Which one is isopentyl alcohol? tert-Pentyl alcohol? (e) Give the structure of a primary, a secondary, and a tertiary alcohol of the formula C,H13OH.arrow_forwardWrite the bond line formula of the following compounds: (a) 4-methyl-2-hexene, two geometrical (stereoisomers) isomers (b) 3-fluoro-2-methylheptanol (3-fluoro-2-methylheptan-1-ol) (c) 4-methyl-hex-1-yn-3-olarrow_forward
- An alkane, P, has the molecular formula, C,H.. An alkene, Q, has the molecular formula, C H,. (a) Name P and Q ánd write their full structural formulae. (b) State two differences between P and Q in terms of their structures. x'arrow_forwardDraw structures that fit each description and name the functional group in each molecule: (a) two constitutional isomers with molecular formula C5H10O that contain different functional groups; (b) two constitutional isomers with molecular formula C6H10O that contain the same functional group.arrow_forward(b) Draw structural formulas of at least two alkynes of each molecular formula.(1) C6H10arrow_forward
- (a) What structural feature is associated with each type of hydrocarbon: alkane, cycloalkane, alkene, and alkyne?(b) Give the general formula for each type.(c) Which hydrocarbons are considered saturated?arrow_forwardDraw structures that t each description and name the functional group in each molecule: (a) two constitutional isomers with molecular formula C5H10O that contain different functional groups; (b) two constitutional isomers with molecular formula C6H10O that contain the same functional group.arrow_forwardWrite Lewis structures and describe the molecular geometry at each carbon atom in the following compounds:(a) cis-3-hexene(b) cis-1-chloro-2-bromoethene(c) 2-pentyne(d) trans-6-ethyl-7-methyl-2-octenearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License