ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
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Chapter 4, Problem 4.66P
Interpretation Introduction
Interpretation:
All the constitutional isomers of
Concept introduction:
Different compounds that have the same molecular formula are classified as isomers.
Constitutional isomers have the same molecular formula. They differ in the connectivity of the atoms. They do not interconvert and can be separated from each other. For substituted cyclohexane, the isomer having substituents at the equatorial position is most stable. Preferably the bulkier groups are more stable at the equatorial position than axial due to reduced in
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Draw all constitutional isomers of all-cis ethylmethylisopropylcyclohexane—that is, in which a methyl group (CH3), an ethyl group (CH2CH3), and an isopropyl group [CH(CH3)2] are all bonded to a cyclohexane ring on the same side of the ring’s plane. Which of those isomers do you think is the most stable? Explain
1. a. Draw and name the five cycloalkane structures of formula C5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers.
b. Draw and name the eight cycloalkane structures of formula C6H12 that do not show geometric isomerism.
c. Draw and name the four cycloalkanes of formula C6H12 that do have cis-trans isomers.
2. Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description.
(a) an isopropylheptane (b) a diethyldecane (c) a cis-diethylcyclohexane
(d) a trans-dihalocyclopentane (e) a (2,3-dimethylpentyl)cycloalkane (f) a bicyclononane
3. 2. refer to the photo attached and answer the ff.3-33, 3-34
Draw the structure of the following molecules, for which the name is given.
1. most stable conformation of 1,1-dichloro-2-bromoethane
2. N,N-Dimethylacetamide
3. cyclooctatetraene
4. bicyclo[2.2.1]heptane
5. spiro[2.4]heptane
Chapter 4 Solutions
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - Prob. 4.3PCh. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Prob. 4.8PCh. 4 - Prob. 4.9PCh. 4 - Prob. 4.10P
Ch. 4 - Prob. 4.11PCh. 4 - Prob. 4.12PCh. 4 - Prob. 4.13PCh. 4 - Prob. 4.14PCh. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Prob. 4.17PCh. 4 - Prob. 4.18PCh. 4 - Prob. 4.19PCh. 4 - Prob. 4.20PCh. 4 - Prob. 4.21PCh. 4 - Prob. 4.22PCh. 4 - Prob. 4.23PCh. 4 - Prob. 4.24PCh. 4 - Prob. 4.25PCh. 4 - Prob. 4.26PCh. 4 - Prob. 4.27PCh. 4 - Prob. 4.28PCh. 4 - Prob. 4.29PCh. 4 - Prob. 4.30PCh. 4 - Prob. 4.31PCh. 4 - Prob. 4.32PCh. 4 - Prob. 4.33PCh. 4 - Prob. 4.34PCh. 4 - Prob. 4.35PCh. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Prob. 4.39PCh. 4 - Prob. 4.40PCh. 4 - Prob. 4.41PCh. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - Prob. 4.47PCh. 4 - Prob. 4.48PCh. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - Prob. 4.51PCh. 4 - Prob. 4.52PCh. 4 - Prob. 4.53PCh. 4 - Prob. 4.54PCh. 4 - Prob. 4.55PCh. 4 - Prob. 4.56PCh. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Prob. 4.61PCh. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - Prob. 4.64PCh. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Prob. 4.68PCh. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Prob. 4.73PCh. 4 - Prob. 4.1YTCh. 4 - Prob. 4.2YTCh. 4 - Prob. 4.3YTCh. 4 - Prob. 4.4YTCh. 4 - Prob. 4.5YTCh. 4 - Prob. 4.6YTCh. 4 - Prob. 4.7YTCh. 4 - Prob. 4.8YTCh. 4 - Prob. 4.9YTCh. 4 - Prob. 4.10YTCh. 4 - Prob. 4.11YTCh. 4 - Prob. 4.12YTCh. 4 - Prob. 4.13YTCh. 4 - Prob. 4.14YTCh. 4 - Prob. 4.15YTCh. 4 - Prob. 4.16YTCh. 4 - Prob. 4.17YTCh. 4 - Prob. 4.18YTCh. 4 - Prob. 4.19YTCh. 4 - Prob. 4.20YTCh. 4 - Prob. 4.21YTCh. 4 - Prob. 4.22YTCh. 4 - Prob. 4.23YTCh. 4 - Prob. 4.24YTCh. 4 - Prob. 4.25YT
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- Draw the most stable conformation of pentane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper, respectively.arrow_forwardThere are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forwardTrue or false Since the energy of the C-H bond is 416 kj/mol and the energy of the C=0rs bond is 678.5Kj/mol, it can be inferred that methanal is more reactive than methane.arrow_forward
- 2.Draw and name the seven constitutional isomers (i.e., all contain a ring of some size) for cycloalkane, C6H12.arrow_forwardWhich cycloalkanes show cis,trans isomerism? For each that does, draw the cis and trans isomers. Q.) 1,1-Dimethylcyclopentanearrow_forwardDraw and name the four cycloalkanes of formula C6H12 that do have cis-trans isomers.arrow_forward
- Draw chair forms for all possible stereoisomers of the following and Write IUPAC names and include cis-tran a) Chlorocyclohexane (b) 1,2-Dichlorocyclohexane(c) 1,3-Dichlorocyclohexane (d) 1,4-Dichlorocyclohexaarrow_forwardChemistry Determine how many substituents in the axial position does the most stable conformer of (1R,2S,4R)-4-bromo-1,2-dimethylcyclohexane have?arrow_forwardDraw all possible structure(s) and give the IUPAC systematic name(s) of an alkane or cycloalkane with the formula C8H18 that has only primary hydrogen atoms...arrow_forward
- Cyclohexane has ________ fewer hydrogens than n-hexane. A) 0 B) 1 C) 2 D) 3 E) 4arrow_forwardClassify the following hydrocarbons as alkanes, cycloalkane, alkene, cycloalkenes, alkyne, cycloalkyne, or aromatic.a. CH2 CH CH2b. CH3 C (CH3)2 CH (CH2CH3) CH2 CH2 CH (CH3)2c. (CH3)3 C C C CH (CH3) CH2 CH3arrow_forwardWhy can’t molecules with the following formulas exist? Please explain briefly for each. a. CH5 b.C2H6N c. C2H2Oarrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License