5. LComplete the multi-step synthesis below by filling in the missing reagents in boxes (a)through (g). Write neatly, and remember that some steps may require more than one step, ora particular type of solvent, etc.OHBr(a)(b)(c)но2CuLi(d)(e)Why is it so important to use only dry glassware and solvents when you hope to perform anutieopnilic attack with an organolithium or organomagnesium reagent?(b) Provide a balanced equation as an example of a reaction which purposefully uses this particular traitof organometallic reagents to our chemical advantage. What epoxide and organometallic reagent are needed to synthesize each alcohol below?Pay close attention to the correct representation of stereochemistry, where appropriate.3.(а)"OHdesiredерохideorganometallic reagentproduct(b)Hноdesiredproductероxideorganometallic reagent4.A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in hisradiator this winter. He proposes the following reaction to his instructor, who quickly explains that thisreaction won't work as proposed due to the student's choice of reagent.1) NaH2) H2OOHНоa) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above?b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give thedesired ethylene glycol product.

Answered: Image /qna-images/answer/e7ec21de-04ed-46fb-8e78-07c3c706ccb8.jpg

5. Complete the multi-step synthesis below by filling in the missing reagents in boxes (a) through (g). Write neatly, and remember that some steps may require more than one step, or a particular type of solvent, etc. to to OH (a) (b) (c) Но 2CuLi (e) (d)

5. Complete the multi-step synthesis below by filling in the missing reagents in boxes (a) through (g). Write neatly, and remember that some steps may require more than one step, or a particular type of solvent, etc. to to OH (a) (b) (c) Но 2CuLi (e) (d)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution

Section16.SE: Something Extra

Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...

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Question

5. L
Complete the multi-step synthesis below by filling in the missing reagents in boxes (a)
through (g). Write neatly, and remember that some steps may require more than one step, or
a particular type of solvent, etc.
OH
Br
(a)
(b)
(c)
но
2CuLi
(d)
(e)
Why is it so important to use only dry glassware and solvents when you hope to perform a
nutieopnilic attack with an organolithium or organomagnesium reagent?
(b) Provide a balanced equation as an example of a reaction which purposefully uses this particular trait
of organometallic reagents to our chemical advantage.

What epoxide and organometallic reagent are needed to synthesize each alcohol below?
Pay close attention to the correct representation of stereochemistry, where appropriate.
3.
(а)
"OH
desired
ерохide
organometallic reagent
product
(b)
H
но
desired
product
ероxide
organometallic reagent
4.
A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his
radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this
reaction won't work as proposed due to the student's choice of reagent.
1) NaH
2) H2O
OH
Но
a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above?
b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the
desired ethylene glycol product.

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