Organic Chemistry 6th Edition solutions

Organic Chemistry 6
Draw a structural formula for a hydrocarbon with the given molecular formula that undergoes hydroboration-oxidation to give the indicated product. 1. (sia)2BH 2. H2O2, NaOH (a) C7H10 H O 1. BH3 OH 2. H2O2, NaOH (b) C7H12

Organic Chemistry 6
Hydration of 2-pentyne gives a mixture of two ketones, each with the molecular formula C5H10O. Propose structural formulas for these two ketones and for the enol from which each is derived.

Organic Chemistry 6
Show how the synthetic scheme in Example 7.6 might be modified to give the following. (a) 1- Heptanol (b) 2-Heptanol

Organic Chemistry 6
Enanthotoxin is an extremely poisonous organic compound found in hemlock water dropwart, which is reputed to be the most poisonous plant in England. It is believed that no British plant has been responsible for more fatal accidents. The most poisonous part of the plant is the roots, which resemble sm

Organic Chemistry 6
Show how to prepare each alkyne from the given starting material. In part (c), D indicates deuterium. Deuterium-containing reagents such as BD3, D2O, and CH3COOD are available commercially. (a) (b) D (c)

Organic Chemistry 6
If a catalyst could be found that would establish an equilibrium between 1,2-butadiene and 2-butyne, what would be the ratio of the more stable isomer to the less stable isomer at 25C? CH2" C " CHCH3 EF CH3C # CCH3 DG 5 216.7 kJ (24.0 kcal)/mol

Organic Chemistry 6
Complete each acid-base reaction, and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3C#CH 1 CH3CH2O2Na1 CH3CH3OH (b) CH3C#CCH2CH2OH 1 Na1NH2 2 NH3(l) (c) CH3C#C2Na1 1 CH3COH O

Organic Chemistry 6
Draw structural formulas for the major product(s) formed by reaction of 3-hexyne with each of these reagents. (Where you predict no reaction, write NR.) (a) H2 (excess)/Pt (b) H2/Lindlar catalyst (c) Na in NH3(l) (d) BH3 followed by H2O2/NaOH (e) BH3 followed by CH3COOH (f) BH3 followed by CH3COOD (g

Organic Chemistry 6
Draw the structural formula of the enol formed in each alkyne hydration reaction, and then draw the structural formula of the carbonyl compound with which each enol is in equilibrium. (a) CH3(CH2)5C#CH 1 H2O (an enol) 9: (b) CH3(CH2)5C#CH 999999999: (an enol) 9: 1. (sia)2BH 2. NaOH/H2O2

Organic Chemistry 6
Propose a mechanism for this reaction. HgSO4 H2SO4 Acetylene HC#CH 1 CH3COH Acetic acid Vinyl acetate O CH3COCH"CH2 O Vinyl acetate is the monomer for the production of poly(vinyl acetate), the major use of which is as an adhesive in the construction and packaging industry, but it is also used in the

Organic Chemistry 6
Show how to convert 9-octadecynoic acid to the following. O OH 9-Octadecynoic acid 18 9 1 (a) (E)- 9-Octadecenoic acid (eliadic acid) (b) (Z)-9-Octadecenoic acid (oleic acid) (c) 9,10- Dihydroxyoctadecanoic acid (d) Octadecanoic acid (stearic acid)

Organic Chemistry 6
For small-scale and consumer welding applications, many hardware stores sell cylinders of MAAP gas, which is a mixture of propyne (methylacetylene) and 1,2-propadiene (allene), with other hydrocarbons. How would you prepare the methylacetylene/ allene mixture from propene in the laboratory?

Organic Chemistry 6
Show reagents and experimental conditions you might use to convert propyne into each product. (Some of these syntheses can be done in one step; others require two or more steps.) Br Br Br Br O CH3C9CH Br Br CH3CCH3 CH3CCH3 O (a) (b) (c) (d) CH3CH2CH

Organic Chemistry 6
Show reagents and experimental conditions you might use to convert each starting material into the desired product. (Some of these syntheses can be done in one step; others require two or more steps.) (a) (b) O (c) HO OH HO OH (d)

Organic Chemistry 6
Show how to convert 1-butyne to each of these compounds. (a) CH3CH2C # C2Na1 (b) CH3CH2C # CD (c) C C (d) H D CH3CH2 H C C H H CH3CH2 D

Organic Chemistry 6
Rimantadine was among the fi rst antiviral drugs to be licensed in the United States for use against the infl uenza A virus and in treating established illnesses. It is synthesized from adamantane by the following sequence (we discuss the chemistry of Step 1 in Chapter 8 and the chemistry of Step 5 i

Organic Chemistry 6
Show reagents and experimental conditions to bring about the following transformations. C C H3C Br Br CH3 C C H3C H H CH3 C C H3C H CH3 H (a) (b) (f) (g) (c) O CH3CCH2CH3 Br CH3CHCH3 Cl Cl CH3CHCH2 Cl CH3C#CH CH3C"CH2 CH3C#CCH3 CH3CH"CH2 (d) (j) (h) (i) Cl Cl CH3CCH3 (e)

Organic Chemistry 6
Show reagents to bring about each conversion. O Br (a) (b) (f) (d) (e) (c) H O

Organic Chemistry 6
Propose a synthesis for (Z)-9-tricosene (muscalure), the sex pheromone for the common housefl y (Musca domestica), starting with acetylene and haloalkanes as sources of carbon atoms. 1 9 10 23

Organic Chemistry 6
Propose a synthesis of each compound starting from acetylene and any necessary organic and inorganic reagents. (a) 4-Octyne (b) 4-Octanone (c) cis-4-Octene (d) trans-4-Octene (e) 4-Octanol (f ) meso-4,5-Octanediol

Organic Chemistry 6
Show how to prepare each compound from 1-heptene: (a) 1,2-Dichloroheptane (b) 1-Heptyne (c) 1- Heptanol (d) 2-Octyne (e) cis-2-Octene (f ) trans-2-Octene

Organic Chemistry 6
Show how to bring about this conversion.

Organic Chemistry 6
Alkyne anions react with the carbonyl groups of aldehydes and ketones to form alkynyl alcohols, as illustrated by the following sequence. HCl H2O CH3C#C2Na1 1 H9C9H [CH3C#C9CH2O2Na1] CH3C#C9CH2OH O Propose a mechanism for the formation of the bracketed compound, using curved arrows to show the fl ow

Organic Chemistry 6
Following is the structural formula of the tranquilizer meparfynol (Oblivon). HO Oblivon Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)

Organic Chemistry 6
The standard procedure for synthesizing a compound is the stepwise progress toward a target molecule by forming individual bonds through single reactions. Typically, the product of each reaction is isolated and purifi ed before the next reaction in the sequence is carried out. One of the ways Nature

Organic Chemistry 6
Use the roadmap you made for problem 6.54 and update it to contain the reactions in the Key Reactions section of this chapter. Because of their highly specifi c nature, do not use reactions 1 and 6 from this chapter on your roadmap.

Organic Chemistry 6
Write the products of the following sequences of reactions. Refer to your roadmap to see how the combined reactions allow you to navigate between the different functional groups. For example, in part (a) below, notice how the reaction sequence results in the conversion of an alkyne into a haloalkane

Organic Chemistry 6
Using your roadmap as a guide, show how to convert acetylene and bromoethane into 1-butene. All of the carbon atoms of the target molecule must be derived from the given starting materials. Show all intermediate molecules synthesized along the way. ? Br Acetylene Bromoethane 1-Butene 1

Organic Chemistry 6
Using your roadmap as a guide, show how to convert ethylene into 1-butene. All of the carbon atoms of the target molecule must be derived from ethylene. Show all intermediate molecules synthesized along the way

Organic Chemistry 6
Using your roadmap as a guide, show how to convert 3-hexyne into propanal. All of the carbon atoms of the target molecule must be derived from the starting material as effi ciently as possible. Show all intermediate molecules synthesized along the way

Organic Chemistry 6
Using your roadmap as a guide, show how to convert the starting trans alkene to the cis alkene in high yield. Show all intermediate molecules synthesized along the way

Organic Chemistry 6
Functional groups such as alkynes react the same in complex molecules as they do in simpler structures. The following examples of alkyne reactions were taken from syntheses carried out in the research group of E. J. Corey at Harvard University. You can assume that the reactions listed involve only th