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Predicting Products from Multistep Syntheses II

Draw the major product from each of the reaction sequences shown below.
To draw a formula use the Drawing Window on the left. When you are finished, check your answer by pressing the Check Molecule # button. A help screen is available for the drawing window.




 1.
Structure of gamma-butyrolactone, a five-membered cyclic ester
1)C2H5NH2
2) LiAlH4 in ether
reaction arrow
3) H3O(+)
2.
Structure of diethyl malonate, CH2(CO2C2H5)2
1)NaOC2H5 ; then C6H5CH2CH2-Br
2) H3O(+) & heat
reaction arrow
3) SOCl2 ; then AlCl3 & heat
3.
Structure of methallyl chloride, 3-chloro-2-methyl-1-propene
1)Mg in ether
2) (CH3)2CH-CN
reaction arrow
3) H3O(+)
4.
Structure of ethyl 2-oxocyclohexanecarboxylate (a beta-keto ester)
1)NaOC2H5 ; then C2H5-I
2) H3O(+) & heat
reaction arrow
3) C6H5CHO & NaOH; heat

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