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Unformatted text preview: Chapter 14
Problem Set . How would you prepare the following alcohols using VGrignard reagents? (a) O/\o|_| (b) 3,3-Dimethyl-2-butanol
(c) ©/\/OH (d) W
, ,OH . Show how a Grignard reagent might be used in the following synthesis: 107:0 *4» MOH OH . The alcohol shown below is used in making perfumes. Outline a synthesis of this
alcohol using reactions you have learned in this chapter. (Hint: Use
bromobenzene as one of your starting materials) Q“ OH . Meparfynol is a mild hypnotic. Outline a synthesis of racemic Meparfynol starting
with compounds of four carbon atoms of fewer. Q7».
(Meparfynol) . Using a Grignard reagent, show how you would synthesize the following
compound from allyl bromide. OH M 6. Draw the organic products you would isolate from the following reactions (after
O (a) CH3Mg| + d
OH (d) M9. 0
A + CVH
(e) O QMQB’ + Ph/U\Ph (f) (CH2=CH)2CuLi + . CH3CH2CH=CHCH2Br 7. Grignard reagents react slowly with oxetane (4-membered ring containing oxygen)
to produce primary alcohols. Show the mechanism of this reaction. R-Mg-X + E10 —————> R\/\/0H (primary alcohol) 8. How would you accomplish the following conversion? mam 9. What is the product of the following reaction? 0
O 1) ZCH3MgBr ———._.__> 2) H30+ 10. .
a) Which of the following has the largest acid dissociation constant K3?
1) CH3CH3 2) H2C=CH2 3) HC-zCH 4) CH3CH20H b) Select the strongest base in the following. 1) NaNHz 2) CHng 3) NaOCH2CH3 4) HCECNa
c) The reaction of excess Grignard reagent with an ester of formic acid, HCOzR,
1) a primary alcohol 2) a tertiary alcohol 3) a secondary alcohol
(1) Reaction of excess Grignard reagent with diethyl carbonate, shown below, gives
/\O/U\O/\ l) ketone 2) tertiary alcohol 3) secondary alcohol 4) ester. e) What is the product of the reaction shown below? Li, 0°C CUI, 'ZOOC CH3(CH2)3CHzBr CH3CH20H2CHzBr ————-> ———-——> ____.—> diethyl ether THF ,7 .,,._--n;,"__r___'rr ,,,.,;',_;_,,,,.1_ iii 14;, :: ,f. -, P” ,1" " tram: I"; Ethan/l, , ...
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- Spring '07
- Organic chemistry