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1) Pentano-5-lactone with methyl iodide

Draw the product of the following reaction of pentano-5-lactone.



(Enciphered hint 1: Bmlzmbujpo jo uif bmgb-qptjujpo pg uif ftufs hspvq.)

2) Haloform reaction 1

Draw all the organic products of the reaction of acetophenone (methyl phenyl ketone) with bromine in the presence of sodium hydroxide (after consequent acidification of the reaction).



(Enciphered hint 1: Evsjoh ibmpgpsn sfbdujpo, cspnjobujpo pg nfuizm hspvq gpmmpxfe cz dmfbwbhf pg uif cpoe cfuxffo uif dbscpozm hspvq boe uif bmgb dbscpo bupn.)

3) Halogenation of acetone

Write enol form of acetone and the product of its reaction with bromine in acetic acid.


(Enciphered hint 1: Ubvupnfsjd gpsn pg bdfupof.)


(Enciphered hint 1: Fopm gpsn pg bdfupof voefshpft uif sfbdujpo xjui fmfduspqijmjd cspnjof.)


4) Butanoic acid with bromine

Draw the product of the following reaction of butanoic acid.



(Enciphered hint 1: Bmqib ibmphfobujpo. Ifmm-Wpmibse-[fmjotlz sfbdujpo.)

5) Cyclohexanone with chlorine

Draw the product of the reaction of cyclohexanone with chlorine in an aqueous medium.



(Enciphered hint 1: Tvctujuvujpo po uif bmqib dbscpo ublft qmbdf.)

6) Enolates 1

Describe the mechanism of the reaction of acetone with hydroxide ion in an aqueous medium and the formation of enolate.



(Enciphered hint 1: Bdje-cbtf frvjmmjcsjvn.)


(Enciphered hint 1: Sftpobodf tusvduvsf.)

7) Haloform reaction 2

Draw all the products of the reaction of tert-butyl methyl ketone with bromine in the presence of sodium hydroxide.



(Enciphered hint 1: Evsjoh ibmpgpsn sfbdujpo, cspnjobujpo pg nfuizm hspvq gpmmpxfe cz dmfbwbhf pg uif cpoe cfuxffo uif dbscpozm hspvq boe uif bmgb dbscpo bupn.)

8) Cyclohexanecarboxylic acid with bromine

Draw the product of the following reaction of cyclohexanecarboxylic acid.



(Enciphered hint 1: Bmqib ibmphfobujpo. Ifmm-Wpmibse-[fmjotlz sfbdujpo.)

9) Alkylation of enolate

Draw the product of the following reaction.



(Enciphered hint 1: Bmlzmbujpo pg bo fopmbuf ublft qmbdf.)

10) Cyclohexanecarbaldehyde with bromine

Draw the product of the reaction of cyclohexanecarbaldehyde with bromine in chloroform.



(Enciphered hint 1: Tvctujuvujpo po uif bmqib dbscpo ublft qmbdf.)

11) Halogenation of cyclopentanone

An enol form of cyclopentanone is formed in the first step of brominantion of cyclopentanone in acetic acid. Draw the formula of enol form and then the product of its bromination.

(Enciphered hint 1: Ubvupnfsjd gpsn pg dzdmpqfoubopof.)


(Enciphered hint 1: Fmfduspqijmjd gpsn pg dzdmpqfoubopof sfbdu xjui fmfduspqijmjd cspnjof.njof.)

12) Leucine via acetamidomalonate (Galat) synthesis

Diethyl acetamidomalonate reacts with isobutyl bromide under basic conditions. The formed compound is then hydrolyzed under acidic conditions. Fill in the products of both reactions.



(Enciphered hint 1: Bmlzmbujpo pg bo fopmbuf gpsnfe jo uif gjstu tufq.)


(Enciphered hint 1: Izespmztjt pg cpui ftufs hspvqt boe uif bnjef hspvq ublft qmbdf boe ju jt gpmmpxfe cz efdbscpyzmbujpo.)

13) Alkylation of enolate 2

Draw the product of the following reaction.



(Enciphered hint 1: Bmlzmbujpo jo uif bmgb-qptjujpo pg uif ojusjmf hspvq.)

14) Enolates 2

Write the equation for the reaction of 2-methyl-1,3-cyclopentadione with hydroxide anion. First, draw the formation of a carbanion.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)


(Enciphered hint 1: Sftpobodf tusvduvsf.)

15) Phenylalanine via acetamidomalonate (Galat) synthesis

Diethyl acetamidomalonate reacts with benzyl bromide under basic conditions. The formed compound is then hydrolyzed under acidic conditions. Fill in the products of the reactions.



(Enciphered hint 1: Bmlzmbujpo pg bo fopmbuf gpsnfe jo uif gjstu tufq.)


(Enciphered hint 1: Izespmztjt pg cpui ftufs hspvqt boe uif bnjef hspvq ublft qmbdf boe ju jt gpmmpxfe cz efdbscpyzmbujpo.)

16) Ethyl acetoacetate 2

Draw ethyl acetoacetate and the product of its reaction with two equivalents of LDA.


(Enciphered hint 1: Fuizm 3-pypcvubopbuf.)


(Enciphered hint 1: Epvcmf efqspupobujpo.)

17) Enamine with methyl iodide

Draw the product of the reaction of cyclopentanone with diethylamine, followed by the reaction with methyl iodide.



(Enciphered hint 1: Fobnjoft bsf gpsnfe cz uif sfbdujpo pg tfdpoebsz bnjoft xjui lfupoft.)


(Enciphered hint 1: Fobnjof bmlzmbujpo jo uif bmgb-qptjujpo jt gpmmpxfe cz gbtu izespmztjt pg uif jnjojvn tbmu.)