Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Question
Chapter 10, Problem 10.48P
Interpretation Introduction
(a)
Interpretation: The structure of stereoisomer that has higher melting point than eleostearic acid is to be drawn.
Concept introduction: Fatty acids are of two types: saturated fatty acid and unsaturated fatty acid. In Saturated fatty acid, double bond is absent, whereas unsaturated fatty acid consists of one or more than one double bond. The melting point of a fatty acid indirectly depends upon the number of double bond present in an acid. Higher is the number of double bonds in acid, lower will be the melting point of an acid.
When two higher priority groups are present on the opposite side then it is an
Interpretation Introduction
(b)
Interpretation: The structure of stereoisomer that has lower melting point is to be drawn.
Concept introduction: Fatty acids are of two types: saturated fatty acid and unsaturated fatty acid. In Saturated fatty acid, double bond is absent, whereas unsaturated fatty acid consists of one or more than one double bond. The melting point of a fatty acid indirectly depends upon the number of double bond present in an acid. Higher is the number of double bonds in acid, lower will be the melting point of an acid.
When two higher priority groups are present on the opposite side, then it is an
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Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oii tree (Aleurites fordii), a deciduous tree
native to China. (a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid. (b) Draw the
structure of a stereoisomer that has a lower melting point.
CO,H
eleostearic acid
(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional
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2-methylcyclohexanone
Chondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacific Ocean.
(a) Predict the solubility of chondrocole A in water and CH2Cl2.
(b) Locate the stereogenic centers and label each as R or S.
(c) Draw a stereoisomer and a constitutional isomer of chondrocole A.
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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- A is a toxin produced by the poisonous seaweed Chlorodesmis fastigiata. (a) Label each alkene that exhibits stereoisomerism as E or Z. (b) Draw a stereoisomer of A that has all Z double bonds.arrow_forwardThe cis ketone A is isomerized to a trans ketone B with aqueous NaOH. A similar isomerization does not occur with ketone C. (a) Draw the structure of B using a chair cyclohexane. (b) Label the substituents in C as cis or trans, and explain the difference in reactivity.arrow_forward(a) Give the IUPAC name for A and B. (b) Draw the product formed when A or B is treated with each reagent: [1] NaBH4, CH3OH; [2] CH3MgBr, then H2O; [3] Ph3P=CHOCH3; [4] CH3CH2CH2NH2, mild acid; [5] HOCH2CH2CH2OH, H+.arrow_forward
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- (a) Which compounds (B–F) are identical to A? (b) Which compounds (B–F) represent an isomer of A?arrow_forwardThe cis ketone A is isomerized to a trans ketone B with aqueous NaOH. Asimilar isomerization does not occur with ketone C. (a) Draw thestructure of B using a chair cyclohexane. (b) Label the substituents in Cas cis or trans, and explain the difference in reactivity.arrow_forward(a) Label the acetal in salicin, a naturally occurring pain reliever isolated from the bark of the willow tree. (b) How many 1° OH groups does salicin contain?arrow_forward
- (a) which if the structure of trans-1,2-dimethylcyclopentane? (b) which is the most stable conformation of 1-bromo-2-ethylcyclohexane? (c) which is the least stable conformation of 1-bromo-2-ethylcyclohexane? (d) which is the more stable configuration of 1,3-dimethylcyclopentane? *Et = ethylarrow_forwardExplain why A is less water soluble than B, even though both compounds have the same functional groups.arrow_forward(a) Add curved arrows for each step to show how A is converted to the epoxy ketone C. (b) Classify the conversion of A to C as a substitution, elimination, or addition. (c) Draw one additional resonance structure for B.arrow_forward
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