PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Question
Chapter 10, Problem 10.45P
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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(a) Draw two different enol tautomers of 2-methylcyclohexanone. (b) Draw two constitutional
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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.
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Chapter 10 Solutions
PKG ORGANIC CHEMISTRY
Ch. 10 - Prob. 10.1PCh. 10 - Problem 10.2 How many degrees of unsaturation are...Ch. 10 -
Problem 10.3 How many degrees of unsaturation...Ch. 10 - Give the IUPAC name for each alkene. abcdeCh. 10 - Give the IUPAC name for each polyfunctional...Ch. 10 - Problem 10.6 Label each C-C double bond as E or Z....Ch. 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 - Problem 10.13 What product is formed when each...Ch. 10 - Prob. 10.14PCh. 10 - Problem 10.15 Draw the products formed when each...Ch. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Addition of HBr to which of the following alkenes...Ch. 10 - Problem 10.19 Draw the products, including...Ch. 10 - Prob. 10.20PCh. 10 - Problem 10.21 What two alkenes give rise to each...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 - Problem 10.26 What alkylborane is formed from...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. 10.29PCh. 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. 10.34PCh. 10 - 10.35 Calculate the number of degrees of...Ch. 10 - Prob. 10.36PCh. 10 - Label the alkene in each drug as E or Z....Ch. 10 - Give the IUPAC name for each compound. a. c. e. b....Ch. 10 - Prob. 10.39PCh. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 10.41PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 10.43PCh. 10 - Prob. 10.44PCh. 10 - Prob. 10.45PCh. 10 - Draw the products formed when (CH3)2C=CH2 is...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 10.48PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 10.50PCh. 10 - Draw all stereoisomers formed in each reaction. a....Ch. 10 - Draw the products of each reaction, including...Ch. 10 - Prob. 10.53PCh. 10 - Prob. 10.54PCh. 10 - Prob. 10.55PCh. 10 - 10.56 Draw a stepwise mechanism for the following...Ch. 10 - Prob. 10.57PCh. 10 - Draw a stepwise mechanism for the conversion of...Ch. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 10.61PCh. 10 - Prob. 10.62PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - 10.65 Draw a synthesis of each compound from...Ch. 10 - 10.66 Explain why A is a stable compound but B is...Ch. 10 - Prob. 10.67PCh. 10 - Prob. 10.68PCh. 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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- Which compounds (B–F) are identical to A? (b) Which compounds (B–F) represent an isomer of A?arrow_forwardChondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacic 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.arrow_forwardDraw the molecule that corresponds to each IUPAC name. (a) 3,3-dipropoxypentan-1-amine; (b) 2,3,4-trichlorocyclohexanol; (c) 3-cyclopropylpentan-1-ol; (d) 3-(1-methylethyl)cycloheptanaminearrow_forward
- Consider the tricyclic structure B. (a) Label each substituent on the rings as axial or equatorial. (b) Draw B using chair conformations for each sixmembered ring. (c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.arrow_forwardAns?arrow_forwardRank each set of compounds in order of increasing boiling points.(a) diethylamine, diisopropylamine, trimethylaminearrow_forward
- The 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) Are compounds B–D identical to or an isomer of A? (b) Give theIUPAC name for A.arrow_forward(a) Are compounds B–D identical to or an isomer of A? (b) Give the IUPAC name for A.arrow_forward
- draw the followingarrow_forward5) Use compounds X, Y and Z (shown below) to answer the following questions. H. H3C" "CH3 ОН CH3 compound X compound Y compound Z a) Is compound X classified as cis, trans or neither? b) Is compound Y classified as E, Z or neither? c) Is compound Z classified as R, S or neither? d) Are compounds X and Y constitutional isomers of each other? (YES or NO) e) Are compounds Y and Z constitutional isomers of each other? (YES or NO) f) Classify compound Y as a primary, secondary or tertiary alcohol. g) Which compound(s) is(are) chiral? h) Give the IUPAC name for compound Z, omitting the absolute configuration (R or S) designation. i) In the indicated spaces below, draw stereoisomers of compounds X, Y and Z. stereoisomer of compound X stereoisomer of compound Y stereoisomer of compound Zarrow_forwardClassify each attached pair of compounds as stereoisomers or conformations: (a) X and Y; (b) X and Z.arrow_forward
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