Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.1, Problem 2P
Draw structures corresponding to the following IUPAC names:
(a) 1, 1-Dimethylcyclooctane
(b) 3-Cyclobutylhexane
(c) 1, 2-Dichlorocyclopentane
(d) l, 3-Dibromo-5-methylcyclohexane
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Draw structures corresponding to the following IUPAC names:
(a) 2-Methyl-1,5-hexadiene
(b) 3-Ethyl-2,2-dimethyl-3-heptene
(c) 2,3,3-Trimethyl-1,4,6-octatriene
(d) 3,4-Diisopropyl-2,5-dimethyl-3-hexene
Draw structures for the following molecules.
(a) 2-iodo-2,3-dimethylheptane
(b) 4-cyclopropyl-3-ethyl-2-methyloctane
(c) 1-ethyl-2,4-dimethylcyclopentane
Draw structures corresponding to the following IUPAC names:
(a) 2-Chloro-3,3-dimethylhexane (b) 3,3-Dichloro-2-methylhexane
(c) 3-Bromo-3-ethylpentane
(e) 4-sec-Butyl-2-chlorononane
(d) 1,1-Dibromo-4-isopropylcyclohexane
() 1,1-Dibromo-4-tert-butylcyclohexane
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- Draw the expanded formula of the following compounds: (a) 3,3-Diethyl-2,5-dimethylnonane (b) 3-Cyclobutylhexane (c) 1,3-Dibromo-5-methylcyclohexanearrow_forwardII. Draw structures corresponding to the following IUPAC names: (a) 3,4-Dimethylnonane (b) 3-Ethyl-4,4-dimethylheptane (c) 2,2-Dimethyl-4-propyloctane (d) 2,2,4-Trimethylpentanearrow_forwardDraw the expanded formula of the following compounds:(a) 4-Ethyl-3, 4-dimethyloctane(b) 1,3-Dibroma-5-methylcyclohexanearrow_forward
- (b) Draw structures corresponding to the following IUPAC names. (a) 3,4-Dimethylnonane (c) 2,2-Dimethyl-4-propyloctane (d) 2,2,4-Trimethylpentane (b) 3-Ethyl-4,4-dimethylheptanearrow_forward1.Draw structures for the following substances: (a) 2-Methylheptane (b) 4-Ethyl-2-methylhexane (c) 4-Ethyl-3,4-dimethyloctane (d) 2,4,4-Trimethylheptanearrow_forwardWrite condensed structures for the following compounds:(a) 4-tert-Butyl-2-methylheptane(b) 2,4-Dimethylpentane(c) 4,4-Diethyl-3-methyloctane(d) 3-Ethyl-1-isopropyl-5-methylcycloheptane(e) 1,1,3-Trimethylcyclopentanearrow_forward
- The following names are incorrect. Write the structural formula that agrees with the apparent name, and then write the correct name of the compound.(a) 2-Ethylbutane(b) 2-Isopropyl-2-methylpentane(c) 5-Ethyl-1,1-methylcyclopentane(d) 3-Ethyl-3,5,5-trimethylhexane(e) 1,2-Dimethyl-4-ethylcyclohexane(f) 2,4-Diethylpentane(g) 5,5,6,6-Methyl-7,7-ethyldecanearrow_forwardDraw the structures corresponding to the following names(a) 2-chloro-3,3-dimethylhexane (b) 3,3-dichloro-2-methylhexane( c) 3-bromo-3-ethylpentane(d) 2-bromo-5-chloro-3-methylhexanearrow_forwardDraw the structure of (a) 4-isopropylheptane (b) 1,1-dichlorocyclopentane (c) cis-3-octenearrow_forward
- Draw structures corresponding to the following IUPAC names 2-Methyl-1,5-hexadiene Explain why each of the following names is incorrect and give the correct name, (a) 2,2-Dimethyl-6-ethylheptane (c) 3-Ethyl-4,4-dimethylhexanearrow_forwardDraw line structures for the following alkenes. Which can exist as cis–trans isomers? For those that can, draw both isomers.(a) 2-Methyloct-2-ene (b) Hept-3-ene(c) 3,4-Dimethylhex-3-enearrow_forwardWhich of the following cycloalkanes are capable of geometric (cis-trans) isomerism?Draw the cis and trans isomers.(a) 3-ethyl-1,1-dimethylcyclohexane (b) 1-ethyl-3-methylcycloheptane(c) 1-ethyl-3-methylcyclopentane (d) 1-cyclopropyl-2-methylcyclohexanearrow_forward
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