Chapter 17: Q50P (page 846)
Number the following compounds in order of increasing pKa value.
Chapter 17: Q50P (page 846)
Number the following compounds in order of increasing pKa value.
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Get started for freePropose a mechanism for the following reaction:
Draw a structure for each of the following:
a. ethyl acetoacetate
b. -methylmalonic acid
c. a -keto ester
d. the enol tautomer of cyclopentanone
e. the carboxylic acid obtained from the malonic ester synthesis when the alkyl halide is propyl bromide
Propose a mechanism for the formation of fructose-1, 6-bisphosphate from dihydroxyacetone phosphate and glyceraldehyde-3-phosphate, using hydroxide ion as the catalyst.
Draw the products of the following reactions:
a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl
b. pentanoic acid + PBr3 + Br2, followed by hydrolysis
c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl
d. diethyl 2-ethylhexanedioate: (1) sodium ethoxide; (2) HCl
e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + ∆
f. acetophenone + LDA/THF: (1) slow addition of diethyl carbonate; (2) HCl
Show how 4-methyl-3-hexanol can be synthesised from 3-pentanone.
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