Organic Chemistry 6th Edition solutions

Organic Chemistry 6
Show how to bring about each conversion using a lithium diorganocopper reagent. I Br (a) (b)

Organic Chemistry 6
Show how to prepare each Gilman reagent in Example 15.4 from an appropriate alkyl halide and each epoxide from an appropriate alkene.

Organic Chemistry 6
Predict the product of the following reaction. CH2 CHBr3 (CH3)3CO2K 1 1 1

Organic Chemistry 6
Show how the following compound could be prepared from any compound containing ten carbons or fewer. OH

Organic Chemistry 6
Complete these reactions involving lithium diorganocopper (Gilman) reagents. ether Br Br ( ( ( ( (CuLi 2 CuLi ether ether CuLi CuLi 2 ( 2 ether 1 1 I 1 ( ( 2 1 (a) (b) (c) (d) "" H C

Organic Chemistry 6
Show how to convert 1-bromopentane to each of these compounds using a lithium diorganocopper (Gilman) reagent. Write an equation, showing structural formulas, for each synthesis.

Organic Chemistry 6
In Problem 15.8, you used a series of lithium diorganocopper (Gilman) reagents. Show how to prepare each Gilman reagent from an appropriate alkyl or vinylic halide.

Organic Chemistry 6
Show how to prepare each compound from the given starting compound through the use of a lithium diorganocopper (Gilman) reagent.

Organic Chemistry 6
The following is a retrosynthetic scheme for the preparation of trans-2-allylcyclohexanol. Show reagents to bring about the synthesis of this compound from cyclohexane. OH (racemic) O Br CH2CH"CH2

Organic Chemistry 6
Complete these equations. diethyl ether O (a) (b) (c) (d) (e) CH3CH2CH2C#CH CH 1 3CH2MgBr diethyl ether Zn(Cu) CH2I 1 2 diethyl ether Zn(Cu) CH2I2 O 1 diethyl ether Zn(Cu) CH2I 1 2 CHBr3 (CH3)3CO2K 1 1 1 CH"CH

Organic Chemistry 6
Reaction of the following cycloalkene with the Simmons-Smith reagent is stereospecifi c and gives only the isomer shown. Suggest a reason for this stereospecifi city. diethyl ether Zn(Cu) CH2I 1 2 H H OH H H OH CH2

Organic Chemistry 6
Show how the following compound can be prepared in good yield. CCl2

Organic Chemistry 6
Show the product of the following reaction (do not concern yourself with which side of the ring is attacked). 1 Zn(Cu) CH2I2 (excess) Caryophyllene H H

Organic Chemistry 6
Show how spiro[2.2]pentane can be prepared in one step from organic compounds containing three carbons or less and any necessary inorganic reagents or solvents. Spiro [2.2] pentane

Organic Chemistry 6
One of the most important uses for Grignard reagents is their addition to carbonyl compounds to give new carbon-carbon bonds (Section 16.5). In this reaction, the carbon of the organometallic compound acts as a nucleophile to add to the positive carbon of the carbonyl. O 1. C6H5MgBr 2. H3O+ (racemic)

Organic Chemistry 6
Organolithium compounds react with carbonyl compounds in a way that is similar to that of Grignard reactions. Suggest a product of the following reaction. O ? 1. CH3Li 2. H3O+ C6H5

Organic Chemistry 6
We now continue the introduction of organic chemistry roadmaps. Because of the many new functional groups that will be introduced in coming chapters, we recommend that you make a new roadmap to accommodate the reactions in Chapters 1518. To make your own roadmap for Chapters 1518, take a blank full s

Organic Chemistry 6
Write the products of the following sequences of reactions. Refer to your roadmaps to see how the combined reactions allow you to navigate between the different functional groups. Note that you will need both your old Chapters 611 roadmap and your new Chapter 15 roadmap for these. (a) 1. Cl2, hn 2. N

Organic Chemistry 6
Using your old and new roadmaps as a guide, show how 1-bromobutane can be converted into either of the two products shown by a suitable choice of reagents. Give reagents and conditions for each reaction. OH ? ? OH Br (racemic)

Organic Chemistry 6
Using your old and new roadmaps as a guide, show how to convert 1-bromo-3- methylbutane into 2,7- dimethyloctane. You must use 1-bromo-3-methylbutane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. 1-Bromo-3-methylbutane 2,7-Dim

Organic Chemistry 6
Using your old and new roadmaps as a guide, show how to convert ethane into 1-butanol. You must use ethane as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way. OH Ethane 1-Butanol ?

Organic Chemistry 6
Using your old and new roadmaps as a guide, show how to convert 1-propanol and diiodomethane into racemic trans-1-methyl-2-propylcyclopropane. You must use 1-propanol and diiodomethane as the source of all carbon atoms in the target molecule. Show all molecules synthesized along the way. OH CH2I 1 2

Organic Chemistry 6
The synthesis of carbohydrates can be particularly diffi cult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate syntheses. Draw the product of the following reactions of a Gilman reagent with each epoxide. (a

Organic Chemistry 6
Gilman reagents are versatile reagents for making new carbon-carbon bonds. Complete the following reactions that use Gilman reagents. (a) Me2CuLi Ether OH (racemic) I O O Me2CuLi Ether 78C to 40C O O O O H O S CF3 (b)