Organic Chemistry 2nd Edition solutions

Organic Chemistry 2
Provide a systematic name for each of the following compounds: (a) (b) Cl Cl (c) Br (d)

Organic Chemistry 2
Draw a bond-line structure for each of the following compounds: (a) 2-Heptyne (b) 2,2-Dimethyl-4- octyne (c) 3,3-Diethylcyclodecyne

Organic Chemistry 2
Predict the product for each of the following reactions: H2 Lindlars catalyst Na NH3 (l) ? H2 Pt ? ?

Organic Chemistry 2
Predict the product for each of the following reactions: H2 Lindlars catalyst H2 Pt ? ?

Organic Chemistry 2
Draw the products of each of the following acid-base reactions and then predict the position of equilibrium in each case: H H + (a) Li @ ! H + NaH (b)

Organic Chemistry 2
Predict the products obtained when 1-pentyne reacts with each of the following reagents: (a) H2SO4, H2O, HgSO4 (b) 9-BBN followed by H2O2, NaOH (c) Two equivalents of HBr (d) One equivalent of HCl (e) Two equivalents of Br2 in CCl4 (f) NaNH2 in NH3 followed by MeI (g) H2, Pt

Organic Chemistry 2
Identify the reagents you would use to achieve each of the following transformations: CH3 O O H Br Br OH O Cl

Organic Chemistry 2
2 Identify which of the following bases can be used to deprotonate a terminal alkyne: (a) NaOCH3 (b) NaH (c) BuLi (d) NaOH (e) NaNH2

Organic Chemistry 2
Identify which of the following compounds represent a pair of keto-enol tautomers: OH O (a) OH O (b) OH O (c) HO OH O OH (d)

Organic Chemistry 2
Draw the enol tautomer of each of the following ketones: O (a) O (b) O (c)

Organic Chemistry 2
Oleic acid and elaidic acid are isomeric alkenes: OH O Oleic acid OH O Elaidic acid Oleic acid, a major component of butter fat, is a colorless liquid at room temperature. Elaidic acid, a major component of partially hydrogenated vegetable oils, is a white solid at room temperature. Oleic acid and el

Organic Chemistry 2
Predict the final product(s) for each sequence of reactions: Br Br 1) Excess NaNH2 2) EtCl 3) H2 (a) , Lindlars catalyst ? H C C H 1) NaNH2 2) MeI 3) 9-BBN 4) H2O2 (b) , NaOH ? H C C H 1) NaNH2 2) EtI 3) HgSO4, H2SO4 (c) , H2O ? H C C H 1) NaNH2 2) MeI 3) NaNH2 4) EtI 5) Na, NH3 (l) ? (d)

Organic Chemistry 2
When (R)-4-bromohept-2-yne is treated with H2 in the presence of Pt, the product is optically inactive. Yet, when (R)-4-bromohex- 2-yne is treated with the same conditions, the product is optically active. Explain.

Organic Chemistry 2
Draw the structure of an alkyne that can be converted into 3-ethylpentane upon hydrogenation. Provide a systematic name for the alkyne.

Organic Chemistry 2
Propose a mechanism for each of the following transformations: (a) NH3 (l) Na HO OH O O H3O+ (b)

Organic Chemistry 2
Draw the expected product of each of the following reactions, showing stereochemistry where appropriate: Cl H D NaNH2 NH3 ?

Organic Chemistry 2
Compound A is an alkyne that reacts with two equivalents of H2 in the presence of Pd to give 2,4,6- trimethyloctane. (a) Draw the structure of compound A. (b) How many chirality centers are present in compound A? (c) Identify the locants for the methyl groups in compound A. Explain why the locants ar

Organic Chemistry 2
Compound A has molecular formula C7H12. Hydrogenation of compound A produces 2- methylhexane. Hydroboration-oxidation of compound A produces an aldehyde. Draw the structure of compound A and draw the structure of the aldehyde produced upon hydroborationoxidation of compound A.

Organic Chemistry 2
Propose a plausible synthesis for each of the following transformations: O (a) (b) Br Br (c) Br Br (d) Cl Cl O Br Br Br Br (e) (f) Cl Cl OH

Organic Chemistry 2
4 1,2-Dichloropentane reacts with excess sodium amide in liquid ammonia (followed by water workup) to produce compound X. Compound X undergoes acid-catalyzed hydration to produce a ketone. Draw the structure of the ketone produced upon hydration of compound X.

Organic Chemistry 2
An unknown alkyne is treated with ozone (followed by hydrolysis) to yield acetic acid and carbon dioxide. What is the structure of the alkyne?

Organic Chemistry 2
Compound A is an alkyne with molecular formula C5H8. When treated with aqueous sulfuric acid and mercuric sulfate, two different products with molecular formula C5H10O are obtained in equal amounts. Draw the structure of compound A, and draw the two products obtained.

Organic Chemistry 2
7 Propose an efficient synthesis for each of the following transformations: (a) (b) O (c) (d)

Organic Chemistry 2
Draw the structure of each possible dichloride that can be used to prepare the following alkyne via elimination:

Organic Chemistry 2
Draw the structures of compounds A to D: A (C6H12) B C 1) Excess NaNH2 2) H2O Br2 NaNH2 D I

Organic Chemistry 2
Identify the reagents necessary to achieve each transformation below. In each case, you will need to use at least one reaction from this chapter and at least one reaction from the previous chapter. The essence of each problem is to choose reagents that will achieve the desired stereochemical outcome:

Organic Chemistry 2
Identify the reagents necessary to achieve each transformation below: D D (a) D D (b) D (c)

Organic Chemistry 2
The following reaction does not produce the desired product but does produce a product that is a constitutional isomer of the desired product. Draw the product that is obtained and propose a mechanism for its formation: OH OH 1) NaNH2 2) MeI

Organic Chemistry 2
Propose a plausible mechanism for the following transformation: O OH O OH H3O+

Organic Chemistry 2
Propose a plausible mechanism for the following tautomerization process: N H CH3 N CH3 H3O+

Organic Chemistry 2
sing acetylene and methyl bromide as your only sources of carbon atoms, propose a synthesis for each of the following compounds: O Et Me + En (a) O Et Me + En (b

Organic Chemistry 2
Propose a plausible mechanism for the following transformation: R R O Br H3O+ Br2

Organic Chemistry 2
Propose a plausible mechanism for the following transformation: D O O H D3O+

Organic Chemistry 2
Roquefortine C belongs to a class of natural products, called roquefortines, first isolated from cultures of the fungus Penicillium roqueforti. Roquefortine C, which is also present in blue cheese, exhibits bacteriostatic activity (it prevents bacteria from reproducing), and it is known to exist as a

Organic Chemistry 2
A small class of natural products, called a,a-disubstituted a-amino acids (Chapter 25), have been the targets of several synthetic techniques, because these compounds are structurally complex (representing a challenge for synthetic organic chemists), and they exhibit notable effects on biological act

Organic Chemistry 2
Natural products that contain the N-1,1-dimethyl-2-propenyl group (called an N-reverse prenyl group) often exhibit antitumor or antifungal activity. The synthesis of a particular N-reverse prenylated indole antifungal compound begins with the two steps shown below (Tetrahedron Lett. 2001, 42, 7277728

Organic Chemistry 2
Treatment of one mole of dimethyl sulfate (CH3OSO3CH3) with two moles of sodium acetylide results in the formation of two moles of propyne as the major product (J. Org. Chem. 1959, 24, 840842): (a) Draw the inorganic, ionic species that is generated as a byproduct of this reaction and show a mechanis

Organic Chemistry 2
Salvinorin A, isolated from the Mexican plant Salvia divinorum, is known to bind with opioid receptors, thereby generating a powerful hallucinogenic effect. It has been suggested that salvinorin A may be useful in the treatment of drug addiction. Terminal alkyne 2, shown below, was used in a total sy

Organic Chemistry 2
Halogenation of alkynes with Cl2 or Br2 can generally be achieved with high yields, while halogenation of alkynes with I2 typically gives low yields. However, the following reaction is successfully completed with I2 in high yields (94%) to afford a potentially useful functionalized and conformational

Organic Chemistry 2
The following compounds exhibit tautomerism, with a particularly high enol concentration. Compound 1 exhibits an enol concentration of 9.1%, as compared with the enol concentration of 0.014% for (CH3)2CHCHO. Compound 2 exhibits an enol concentration of 95% (Acc. Chem. Res. 1988, 21, 442449): 1 2 O H

Organic Chemistry 2
The two lowest energy conformations of pentane are the anti-anti and the anti-gauche forms, in terms of arrangements around the two central C!C bonds. A recent study analyzed the conformations of 3- heptyne as an elongated analogue of pentane, where a carbon-carbon triple bond is inserted between C2

Organic Chemistry 2
A variety of phenyl-substituted acetylenes (1ad) were treated with HCl to give a mixture of E and Z isomers, as shown below (J. Am. Chem. Soc. 1976, 98, 32953300): C C R HCl C C H R Cl + C C R H Cl E:Z Ratio 1a (R = Me) 70:30 1b (R = Et) 80:20 1c (R = i-Pr) 95:5 1d (R = t-Bu) 100:0 1 (a) Draw the two

Organic Chemistry 2
The compound 1,2-bis-(phenylethynyl)benzene (1) undergoes reactions with aqueous acid or bromine, as shown below (J. Am. Chem. Soc. 1966, 88, 45254526). Propose a reasonable arrow- pushing mechanism for both of these reactions. Also provide an explanation for the configuration of the exocyclic alkene