EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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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.
(a) Locate the isoprene units in lycopene, the red pigment in tomatoes. (b) Which isoprene units are connected in a head-to-tail fashion? (c) Label any other isoprene unit as connected in a head-tohead fashion or a tail-to-tail fashion. (d) Classify lycopene as a monoterpene, sesquiterpene, and so on.
Draw the organic products formed when attached compound is treated with H2, Pd-C. Indicate the three-dimensional structure of all stereoisomersformed.
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- C. Draw structures for the following compounds. 2,4-dichloro-3-iodotoluene o-nitroanisole 2-methyl-1-phenylhexane 2,4,6-trinitrotoluenearrow_forward5. Ribose's structure is ОН HO ОН ОН a) Draw using the arrow formalism the reaction of linear ribose to make a 5-membered ring. b) What is the name of the resulting functional group? c) Given that reaction of alcohols (such as RCH2OH) with carbonyls (such as HCO-R') to create this functional group is typically not thermodynamically favored, why does most ribose in water exist as a 5-membered ring? A few word answer is fine. d) AG°for this reaction is about - 5 kJ/mol. Assuming that you start with a 1 mM solution of ribose in water, what is the approximate concentration at equilibrium of (i) the linear form? (ii) The cyclic form? (A good answer should be correct within 20%, e.g. it is fine to approximate 9 mM as 10 mM, but it is not okay to approximate 0.1 mM as 1 mM.) e) This reaction creates a new stereocenter. Please indicate it with a *. f) Consider the starting point for synthesis of purines like ATP, which is PRPP (pheseboribosylevOrhesehate) НО НО LOLOH HO ОН HO OH Pyrophosphate…arrow_forwardThe following chemical reaction is used to synthesize a flavouring agent that has an aroma similar to bananas. H₂SO4(aq) CH3COOH(1) + CH₂(CH₂)₂OH(1) I || Identify the type of reaction that is represented by this synthesis. Select one: O hydrogenation O esterification O addition O substitution O elimination Identify the functional group and the IUPAC name for each of the three compounds in the reaction below: H₂SO4(aq) I Compound Functional Group IUPAC Name II CH₂COOH(1) + CH₂(CH₂)₂OH(1) I || III CH3COO(CH₂)₂CH₂(1) + H₂O(1) III IV ◆ → ◆ CH3COO(CH₂)₂CH₂(1) + H₂O(1) IV ||| ◆ ◆arrow_forward
- Locate the isoprene units in each compound.arrow_forwardOnly three stereoisomers are possible for 2,3-dibromo-2, 3-dichlorobutane. Draw them, indicating which pair are enantiomers (optical isomers). Why does the other isomer not have an enantiomer?arrow_forwardEthers (general formula R—O—R)have many important uses. Until recently,methyl tert-butyl ether (MTBE, right)was used as an octane booster and fueladditive for gasoline. It increases the oxy-gen content of the fuel, which reducesCO emissions. MTBE is synthesized bythe catalyzed reaction of 2-methylpropene with methanol.(a) Write a balanced equation for the synthesis of MTBE. (Hint:Alcohols add to alkenes similarly to the way water does.)(b) If the government required that auto fuel mixtures contain2.7% oxygen by mass to reduce CO emissions, how many gramsof MTBE would have to be added to each 100. g of gasoline?(c) How many liters of MTBE would be in each liter of fuel mix-ture? (The density of both gasoline and MTBE is 0.740 g/mL.)(d) How many liters of air (21% O₂ by volume) are needed at24C and 1.00 atm to fully combust 1.00 L of MTBE?arrow_forward
- Pure acetic acid is a viscous liquid, with high melting and boiling points (16.7 °C and 118 °C) compared to compounds of similar molecular weight. Suggest an explanation.arrow_forwardIdentify the functional groups in two drugs, atenolol and donepezil. Atenololis a β (beta) blocker, a drug used to treat hypertension (high bloodpressure), and donepezil (trade name Aricept) is used to treat mild tomoderate dementia associated with Alzheimer's disease.arrow_forwardFats belong to the class of organic compounds represented by the general formula, RCOOR', where R and R' represent hydrocarbon groups; therefore, fats are: a. ethers. b. soaps. c. esters. d. lipases.arrow_forward
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