Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 5.9, Problem 21P
Interpretation Introduction
Interpretation:
The relationship between this pair of isomers is to be determined.
Concept introduction:
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Which of the following cycloalkanes show cis-trans isomerism? For each thatdoes, draw both isomers.
(a) Methylcyclopentane(c) 1,3-Dimethylcyclobutane
(b) 1,1-Dimethylcyclopentane
The following names are incorrect: State why each name is wrong and give the correct name
3-methyl-3-butene
cis-3-pentene
cis-2-methyl-2-pentene
Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound
may fit into more than one of the following classifications:
alkane
cycloalkane
aromatic hydrocarbon
alkene
cycloalkene
alkyne
cycloalkyne
(a) (CH;CH2);CHCH(CH3)2
(b) CH;CHCHCH,CH3
(c) CH;CCCH,CH,CH3
CH,-C=C-CH
CH, —CH, —CH, —сн
(d)
(e)
CHCH2
(f)
CCH
-
CHC(CH,),
(h)
- CH2CH3
(i)
Chapter 5 Solutions
Organic Chemistry
Ch. 5.2 - Prob. 1PCh. 5.2 - Prob. 2PCh. 5.2 - Prob. 3PCh. 5.2 - Prob. 4PCh. 5.3 - Is cocaine (Worked Example 5-2) dextrorotatory or...Ch. 5.3 - Prob. 6PCh. 5.5 - Prob. 7PCh. 5.5 - Prob. 8PCh. 5.5 - Prob. 9PCh. 5.5 - Assign R or S configuration to the chirality...
Ch. 5.5 - Draw a tetrahedral representation of...Ch. 5.5 - Prob. 12PCh. 5.6 - One of the following molecules (a)–(d) is...Ch. 5.6 - Prob. 14PCh. 5.6 - Assign R or S configuration to each chirality...Ch. 5.7 - Prob. 16PCh. 5.7 - Which of the following have a meso form? (Recall...Ch. 5.7 - Does the following structure represent a meso...Ch. 5.8 - Prob. 19PCh. 5.8 - Prob. 20PCh. 5.9 - Prob. 21PCh. 5.11 - Prob. 22PCh. 5.11 - Prob. 23PCh. 5.11 - The lactic acid that builds up in tired muscles is...Ch. 5.11 - The aconitase-catalyzed addition of water to...Ch. 5.SE - Which of the following structures are identical?...Ch. 5.SE - Prob. 27VCCh. 5.SE - Prob. 28VCCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 30VCCh. 5.SE - Prob. 31APCh. 5.SE - Which of the following compounds are chiral? Draw...Ch. 5.SE - Prob. 33APCh. 5.SE - Eight alcohols have the formula C5H12O. Draw them....Ch. 5.SE - Draw compounds that fit the following...Ch. 5.SE - Prob. 36APCh. 5.SE - Prob. 37APCh. 5.SE - Prob. 38APCh. 5.SE - What is the stereochemical configuration of the...Ch. 5.SE - Prob. 40APCh. 5.SE - Prob. 41APCh. 5.SE - Prob. 42APCh. 5.SE - Prob. 43APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 46APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configurations to the chirality...Ch. 5.SE - Assign R or S stereochemistry to the chirality...Ch. 5.SE - Prob. 50APCh. 5.SE - Draw examples of the following: (a) A meso...Ch. 5.SE - Prob. 52APCh. 5.SE - Prob. 53APCh. 5.SE - Prob. 54APCh. 5.SE - On reaction with hydrogen gas by a platinum...Ch. 5.SE - Prob. 56APCh. 5.SE - Prob. 57APCh. 5.SE - One of the steps in fat metabolism is the...Ch. 5.SE - The dehydration of citrate to yield cis-aconitate,...Ch. 5.SE - The first step in the metabolism of glycerol,...Ch. 5.SE - One of the steps in fatty-acid biosynthesis is the...Ch. 5.SE - Prob. 62APCh. 5.SE - Draw tetrahedral representations of the two...Ch. 5.SE - The naturally occurring form of the amino acid...Ch. 5.SE - Prob. 65APCh. 5.SE - Prob. 66APCh. 5.SE - Prob. 67APCh. 5.SE - Allenes are compounds with adjacent carbon-carbon...Ch. 5.SE - Prob. 69APCh. 5.SE - Prob. 70APCh. 5.SE - How many stereoisomers of...Ch. 5.SE - Draw both cis- and trans-1,4-dimethylcyclohexane...Ch. 5.SE - Draw both cis- and trans-1,3-dimethylcyclohexane...Ch. 5.SE - cis-1,2-Dimethylcyclohexane is optically inactive...Ch. 5.SE - Prob. 75APCh. 5.SE - Prob. 76APCh. 5.SE - Prob. 77AP
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- Below are structural formulas for isomers of butane. What type of isomerism is exemplified by these isomers? What makes (a) cis- and (b) trans-?arrow_forwardUnder topic haloalkanearrow_forwardDraw the following compounds. a) 4-methyl-1,2-pentadiene b) (3E, 5Z)-2,6-dimethyl-1,3,5,7-octatetraenearrow_forward
- The skeletal line formula for a branched alkene is shown below. (i) What is the molecular formula of this compound? (ii) How many carbon atoms are in the longest chain, ignoring the double bond? (iii) What is the longest chain incorporating both carbons of the double bond? (iv) How many substituents are on this chain? (v) Give the IUPAC name for this compound. [6]arrow_forwardDraw the skeletal (bond-line) structures of all isomers of C4H8O (including configurational isomers) that contain an alkene and an ether. There should be 5 structures.arrow_forward(b) 3-Chloro-1,4-hexadiene (R), (Z) isomer name: (S), (Z) isomer name: (R), (E) isomer name: (S), (E) isomer name:arrow_forward
- Write 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_forwardDraw line structures for the following cycloalkanes:(a) 1,1-Dimethylcyclopropane(b) 1,3-Dimethylcyclopentane(c) Ethylcyclohexane(d) Cycloheptane(e) 1-Methyl-3-propylcyclohexane(f) 1-Ethyl-4-isopropylcyclooctanearrow_forwardDraw the structures for the following compounds.(a) 3-benzyl-4-bromohexane , 4,4-dimethylcyclohexene(b) trans-4,5-dibromohex-2-ene , cis-1,1-dibromo-2-ethyl-2,3-dimethylcyclobutanearrow_forward
- • 4-Draw the structures of the following molecules: • a) trans-1-Bromo-3-methylcyclohexane .b) cis-1,2-Dimethylcyclobutanearrow_forwardWhich compound does not exist? (a) 1,2,3,4,5,6,7-octaheptaene (b) cis-2-butane (c) trans-3-hexene (d) 1-propene (e) cis-4-decenearrow_forwardDraw a structural formula for cis-1-bromo-3-ethylcyclopentane. • Show stereochemistry only if given in the name. • In cases where there is more than one answer, just draw one.arrow_forward
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