PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Chapter 10, Problem 10.69P
Lactones, cyclic esters such as compound A, are prepared by halolactonization, an addition reaction to an
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Lactones, cyclic esters such as compound A, are prepared by halolactonization, an addition reaction to an alkene. For example, iodolactonization of B forms lactone C, a key intermediate in the synthesis of prostaglandin PGF2α (Section 4.15). Draw a stepwise mechanism for this addition reaction.
Lactones, cyclic esters such as compound A, are prepared byhalolactonization, an addition reaction to an alkene. For example,iodolactonization of B forms lactone C, a key intermediate in thesynthesis of prostaglandin PGF2α. Draw a stepwise mechanism for this addition reaction.
Which of the isomeric C4H₁0O alcohols can be prepared by hydrogenation of aldehydes?
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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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- The foul odor of rancid butter is caused by butyric acid, CH3CH2CH2CO2H. (a) Draw the Lewis structure and determine the oxidation number and hybridization for each carbon atom in the molecule. (b) The esters formed from butyric acid are pleasant-smelling compounds found in fruits and used in perfumes. Draw the Lewis structure for the ester formed from the reaction of butyric acid with 2-propanol.arrow_forwardName and draw a structural formula for the product of each alkene addition reaction. (a) (b)arrow_forwardSynthesize each compound.You may use benzene, acetylene (HC≡CH), ethanol, ethylene oxide, and any inorganic reagents.arrow_forward
- Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forwardAlkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forwarda) b) d) 4. Draw the correct structure of the alcohol starting material that would give the following oxidized products: H A ora forarrow_forward
- 2. What is the organic by-product in a haloform reaction? A) an ether B) a haloform C) an alcohol D) an ester E) an amidearrow_forwardMany insects utilize cyclic ketal structures as pheromones such as the structure shown below. The biosynthetic pathway involves the cyclization of this acetal from the straight chain structure. Draw the straight chain structure that could be used to form this acetal. Use wedges and dashes to correctly depict the stereochemistry. H3C- >arrow_forward3. Ethanoic acid (vinegar) when diluted to low concentrations by water can be prepared from ethene by a) reduction with H2, followed by reaction with a strong oxidizer b) addition of HCL followed by reaction with H20 c) addition of H20 followed by reaction with a strong oxidizer d) addition of Br2 e) followed by reduction with H2arrow_forward
- Indicate the CORRECT alternative: a) Acid halides react only in the presence of a catalyst. b) The reaction of an acid chloride with an alcohol produces less of an ester than using the Fischer reaction. c) The nucleophilic substitution reaction in acid derivatives occurs through an SN1 mechanism. d) Reduction of an ester with LiAlH4 yields only secondary alcohols. e) Hydrolysis of an amide in an acid medium produces a carboxylic acid and a protonated amine.arrow_forward8) The structural formulae of several carbonyl compounds A to E are shown below. H3C-C-H CH,CCH, CH,CH A) B) CH3 D) E) Which of these compounds a) is oxidised to a carboxylic acid without the loss of any carbon atoms? b) undergoes addition reaction with sodium hydrogen sulphite? c) forms a yellow precipitate when tested with lodine in an alkaline solution? d) forms a silver mirror when tested with Tollen's reagent? e) forms a brick red precipitate when tested with Fehling's solution? f) forms a yellow precipitate when tested with 2,4-dinitrophenylhydrazine?arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. ROH, H+ OH OR Aldehyde/ketone Alcohol ROH, H+ Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds: OH OH OR OR • Use the wedge/hash bond tools to indicate stereochemistry where it exists. + H₂Oarrow_forward
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