Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 10, Problem 10.39P
The fertility drug clomiphene (trade name Clomid) is sold as a mixture of diastereomers, enclomiphene and zuclomiphene. Designate each
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Pyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized
by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides.
CH3
CH2=CH-CH.
CH-C-
-HCS
0-CH,
CH,-C
H2C-
ČH,
Which is not a functional group or structural feature in jasmolin II?
cycloalkane
carboxylic acid
ester
alkene
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
What type of isomerism is exemplified by these isomers? What makes (a) cis- and (b) trans-?
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 10.1PCh. 10 - Problem 10.2 How many degrees of unsaturation are...Ch. 10 - Give an example of a compound with molecular...Ch. 10 - Give the IUPAC name for each alkene.Ch. 10 - Give the IUPAC name for each polyfunctional...Ch. 10 - Prob. 10.6PCh. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Problem 10.10 Rank the following isomers in order...
Ch. 10 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Which compounds A-D in Figure 10.12 are formed by...Ch. 10 - What two alkenes give rise to each alcohol as the...Ch. 10 - Prob. 10.22PCh. 10 - Problem 10.23 Draw the products of each reaction,...Ch. 10 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Borane is sold for laboratory use as a complex...Ch. 10 - What alkylborane is formed from hydroboration of...Ch. 10 - Draw the products formed when each alkene is...Ch. 10 - What alkene can be used to prepare each alcohol as...Ch. 10 - Prob. 10.31PCh. 10 - Draw the products of each reaction using the two...Ch. 10 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 10.36PCh. 10 - Calculate the number of degrees of unsaturation f...Ch. 10 - Prob. 10.38PCh. 10 - The fertility drug clomiphene trade name Clomid is...Ch. 10 - Give the IUPAC name for each compound. a....Ch. 10 - Give the structure corresponding to each name. a....Ch. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.43PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.45PCh. 10 - Prob. 10.46PCh. 10 - Prob. 10.47PCh. 10 - Prob. 10.48PCh. 10 - By using the bond dissociation energies in...Ch. 10 - Prob. 10.50PCh. 10 - Repeat Problem 10.50 with CH32C=CH2 as the...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.53PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.55PCh. 10 - Draw all stereoisomers formed in each reaction....Ch. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59PCh. 10 - Draw a stepwise mechanism for the following...Ch. 10 - Draw a stepwise mechanism for each reaction. a.b.Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.64PCh. 10 - Prob. 10.65PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - Prob. 10.68PCh. 10 - Prob. 10.69PCh. 10 - Prob. 10.70PCh. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.72PCh. 10 - Prob. 10.73PCh. 10 - 10.69 Lactones, cyclic esters such as compound A,...Ch. 10 - 10.70 Draw a stepwise mechanism for the following...Ch. 10 - 10.71 Like other electrophiles, carbocations add...Ch. 10 - 10.72 Draw a stepwise mechanism for the...
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- Distinguish between isomerism and resonance. Distinguish between structural and geometric isomerism. When writing the various structural isomers, the most difficult task is identifying which are different isomers and which are identical to a previously written structurethat is, which are compounds that differ only by the rotation of a carbon single bond. How do you distinguish between structural isomers and those that are identical? Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C4H8. Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one or more bonds in the compound, so both can exhibit cis- trans isomerism. What is required for an alkene or cycloalkane to exhibit cis-trans isomerism? Explain the difference between cis and trans isomers. Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table 21-4 can be structural isomers of carboxylic acids? What is optical isomerism? What do you look for to determine whether an organic compound exhibits optical isomerism? 1-Bromo-1-chloroethane is optically active whereas 1-bromo-2-chloroethane is not optically active. Explain.arrow_forwardIllustrate this phenomenon, compare ethane (CH3CH3), ethylene (CH2=CH2), and acetylene (HC=CH).arrow_forwardOrganic compounds may have characteristic odors as well as other characteristic physical properties. For example, the distinct odor of the seashore at low tide results in part from the presence of dimethyl sulfide (CH3SCH3), a molecule with a similar structure to dimethyl ether (CH3OCH3). Ethanethiol (CH3CH2SH), also called mercaptan, is an isomer of dimethyl sulfide with a much less pleasant odor.The table lists four related compounds and their enthalpies of vaporization (ΔH°vap) in kJ/mol. Compound ΔH°vap (kJ/mol) CH3OCH3 23 CH3SCH3 28 CH3CH2SH 27.5 CH3CH2OH 42 Rank the following compounds in order of increasing strength of their intermolecular forces, given the ΔH°vap listed for each. Place the compound with the strongest intermolecular forces (IMFs) at the top of the list. (Strongest to weaknest). Why is ΔHºvap for CH3SCH3 greater than ΔHºvap for CH3OCH3? A. CH3OCH3 is more polar. B. CH3SCH3 has stronger dipole–dipole attractions. C. CH3OCH3 can form…arrow_forward
- Does tetrahydrocannabinol (C21 H30 O2) have any Alkene functional groups?arrow_forward2. a) Explain what structural feature of the double bond is required for an alkene to exhibit cis-trans (geometric) isomerism? b) Which of the following alkenes can exhibit cis-trans isomerism? If the molecule exhibits cis- trans isomerism, draw and name the associated isomer. 1- pentene CH2=CHCH2CH2CH3 i) ii) 2- pentene CH3CH=CHCH₂CH3 -0arrow_forward1. Draw the constitutional isomers of the molecular formula C6H14 and name each using IUPAC system. A. Which one gives two and only two monobromo derivatives when it reacts with Br2 and light? Name the products using IUPAC system B. Which give three and only three monobromo products? Name the products, using the IUPAC system.arrow_forward
- Draw 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_forwardName the given formulas.arrow_forwardALKENES 1. Compound A, C4H8, has two structural isomers, B and C. Both B and C decolourise bromine dissolved in dichloromethane. B does not exhibit cis-trans isomerism but C does. a) Draw the possible structures of B and C and name them. b) Describe another chemical test to distinguish between B and butane. Write equations and observations involved. c) A has another structural isomer, D, that does not decolourise bromine in dichloromethane when being placed in the dark room. Suggest a structure for D. Explain your answer.arrow_forward
- What is cis-trans isomerism in alkenes? cis-trans isomerism in alkenes involves having the major groups in an alkene on the same or opposite side of the double bond cis-trans isomerism in alkenes involves having different or identical substituents at the both ends of the double bond cis-trans isomerism in alkenes involves having the major groups in an alkene in staggered or eclipsed conformations cis-trans isomerism in alkenes involves different location of double bond along the carbon chainarrow_forwardWhat is the relationship of these two structures?arrow_forwardDraw one isomer structure of cis-diethylcyclohexane.arrow_forward
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