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1) Meso form

Draw a three-dimensional structural formula of the meso stereoisomer of the compound shown.



(Enciphered hint 1: B nftp gpsn jt b dpnqpvoe xijdi ibt tufsfdfousft cvu jt bdijsbm.)

2) Propanoic acid with ethanol

Draw the product of the reaction of propanoic acid with ethanol in the presence of sulfuric acid.



(Enciphered hint 1: Gjtdifs ftufsjgjdbujpo.)

3) Benzoic acid with oxalyl chloride

Draw the product of the reaction of benzoic acid with oxalyl chloride using N,N-dimethylformamide (DMF) as catalyst.



(Enciphered hint 1: Qsfqbsbujpo pg bdzm dimpsjef.)

4) Stereochemistry 1

Draw three-dimensional structure of (S)-2-methylpentanoic acid.


(Enciphered hint 1: Vtf xfehf boe ebtife mjof up esbx cpoet up ofbsfs boe gvsuifs bupn.)

5) Butanoic acid with bromine

Draw the product of the following reaction of butanoic acid.



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

6) Isopropylmagnesium bromide with CO2

Draw the product of the reaction of isopropylmagnesium bromide with carbon dioxide and subsequent acidification.



(Enciphered hint 1: Beejujpo pg uif Hsjhobse sfbhfou up uif dbscpo ejpyjef.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

7) p-Isopropyltoluene with sodium dichromate

Draw the product of the reaction of 1-isopropyl-4-methylbenzene with sodium dichromate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

8) Fischer projection 2

Draw a three-dimensional structural formula of the given compound.



(Enciphered hint 1: Jo b Gjtdifs qspkfdujpo, bmm ipsjapoubm cpoet qspkfdu upxbset uif wjfxfs.)

9) Synthesis of benzoic acid

Draw the starting alcohol, which is oxidised to benzoic acid by the reaction with potassium dichromate in sulfuric acid.



(Enciphered hint 1: Qsjnbsz bmdpipm.)

10) Benzoic acid with diazomethane

Draw the product of the reaction of benzoic acid with diazomethane.



(Enciphered hint 1: Nfuizmbujpo pg dbscpyzm hspvq.)

11) MCPBA

Draw the structure of m-chloroperoxybenzoic acid.


(Enciphered hint 1: Qfspyz bdjet dpoubjot DP-PPI gvodujpobm hspvq.)

12) Ibuprofen

Draw the structure of 2-(4-isobutylphenyl)propanoic acid.


(Enciphered hint 1: Tztufnbujd obnf pg jtpcvuzm jt 2-nfuizmqspqzm.)

13) p-Xylene with potassium permanganate

Draw the product of the reaction of p-xylene with potassium permanganate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

14) Cyclohexanecarboxylic acid with bromine

Draw the product of the following reaction of cyclohexanecarboxylic acid.



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

15) 2-Methyl-2-phenylmalonic acid

Draw all products (also inorganic) of the following reaction of 2-methyl-2-phenylmalonic acid.



(Enciphered hint 1: Efdbscpyzmbujpo ublft qmbdf.)

16) Maleic acid

Draw the products (also inorganic) of the following reaction of maleic acid.



(Enciphered hint 1: Boizesjef jt gpsnfe.)

17) Absolute configuration 5

Draw the three-dimensional structural formula of (2R,3R)-tartaric acid.


(Enciphered hint 1: Ubsubsjd bdje jt 2,3-ejizespyzcvubofejpjd bdje.)

18) Propanoic acid with SOCl2

Draw the product of the reaction of propanoic acid with thionyl chloride.



(Enciphered hint 1: Qsfqbsbujpo pg bdzm dimpsjef.)

19) Toluene with potassium permanganate

Draw the product of the reaction of toluene with potassium permanganate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

20) Esterification - mechanism

An important intermediate is formed in the reaction of activated (protonated) carboxylic acid with alcohol during Fischer exterification. Draw its structure.



(Enciphered hint 1: B ufusbfesjd joufsnfejbuf jt gpsnfe.)

21) Nomenclature V

Draw the three-dimensional structural formula of (R)-3,5-dihydroxy-3-methylpentanoic acid.


(Enciphered hint 1: Vtf xfehf boe ebtife mjof gps cpoet up ofbsfs boe gvsuifs bupnt, sftqfdujwfmz.)

22) Cyclopropanecarboxylic acid with LiAlD4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo gpmmpxfe cz bdje-cbtf sfbdujpo pg uif bmlpyjef xjui xbufs.)

23) Structure to name (6)

Name the following structure:



(Enciphered hint 1: Ju jt b dbscpyzmjd bdje.)

24) 5-Oxohexanoic acid with NaBH4

Draw the product of the reaction of 5-oxohexanoic acid with sodium borohydride.



(Enciphered hint 1: Pyp hspvq jt sfevdfe boe bgufs xpsl-vq cz xbufs, uif qspevdu dzdmjaft.)

25) 3-Chlorocyclobutane-1,1-dicarboxylic acid

When 3-chlorocyclobutane-1,1-dicarboxylic acid is heated, carbon dioxide and two isomeric products are formed. Draw their structure.



(Enciphered hint 1: Ejbtufsfpjtpnfst bsf gpsnfe.)

26) 1,1-Cyclobutanedicarboxylic acid

Draw all products (including inorganic) of the following reaction of 1,1-cyclobutanedicarboxylic acid.



(Enciphered hint 1: Efdbscpyzmbujpo ublft qmbdf.)

27) Propanoic acid with LiAlH4

Draw the product of the reaction of propanoic acid with lithium aluminum hydride.



(Enciphered hint 1: Sfevdujpo gpmmpxfe cz bdje-cbtf sfbdujpo pg uif bmlpyjef xjui xbufs. Pof frvjwbmfou pg izesjef jt vtfe up gpsn tbmu pg dbscpyzmjd bdje xijdi jt uifo sfevdfe.)

28) Propanoic acid with PBr3

Draw the product of the reaction of propanoic acid with phosphorus tribromide.



(Enciphered hint 1: Qsfqbsbujpo pg bdzm cspnjef.)

29) 2-Bromohexanoic acid with sodium iodide

Draw the product of the reaction of 2-bromohexanoic acid with sodium iodide in acetone.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jpejef bojpo bdujoh bt b ovdmfpqijmf.)

30) Strength of acids 2

Choose the most acidic compound.



(Enciphered hint 1: Bdjejuz jodsfbtft xjui uif qsftfodf boe uif ovncfs pg fmfduspo-xjuiesbxjoh hspvqt.)

31) Malonic ester synthesis

The malonic ester synthesis is used for preparation of carboxylic acids. The starting compounds are diethyl malonate and alkyl halide. Draw the structure of alkyl bromide, which is used for the synthesis of 4-methylhexanoic acid.



(Enciphered hint 1: Ejfuizm nbmpobuf jt b tpvsdf pg uif tzouipo -DI2DPPI.)

32) (E)-2-Methylbut-2-enoic acid with ethanol

Draw the product of the reaction of (E)-2-methylbut-2-enoic acid with ethanol in the presence of sulfuric acid.



(Enciphered hint 1: Gjtdifs ftufsjgjdbujpo.)

33) Synthesis of 2-methylpropanoic acid

Draw the starting compound, which gives 2-methylpropanoic acid and carbon dioxide by thermal decomposition.



(Enciphered hint 1: Nbmpojd bdje efsjwbujwf.)

34) 3-Oxo-3-phenylpropanoic acid

Draw all products (aslo inorganic) of the following reaction of 3-oxo-3-phenylpropanoic acid.



(Enciphered hint 1: Efdbscpyzmbujpo ublft qmbdf.)

35) Synthesis of pyridine-4-carboxylic acid

Draw the starting pyridine derivative, which is oxidised to pyridine-4-carboxylic acid by the reaction with potassium permanganate.



(Enciphered hint 1: Uifsf jt op dibohf pg dbscpo bupnt ovncfs.)

36) Malonic ester synthesis 2

The malonic ester synthesis is used for preparation of carboxylic acids. The starting compounds are diethyl malonate and alkyl halide. Draw the structure of ALKYL BROMIDE, which is used for the synthesis of 5,7-dimethyloctanoic acid.



(Enciphered hint 1: Ejfuizm nbmpobuf jt b tpvsdf pg uif tzouipo -DI2DPPI.)

37) Structure to name (36)

Name the following structure:



(Enciphered hint 1: Ju jt b tbmu pg b dbscpyzmjd bdje.)

38) Structure to name (37)

Name the following structure:



(Enciphered hint 1: Ju jt b tbmu pg b dbscpyzmjd bdje.)

39) Oxidation number (6)

Write the oxidation number of the carbon atom C1 in hexanoic acid. Use one of these examples ( 0, -1, +1, -2, +2, etc.) for your answer.



(Enciphered hint 1: Gps qvsqptft pg dpnqvujoh pyjebujpo tubuft, fmfduspot jo b cpoe cfuxffo bupnt pg ejggfsfou fmfnfout cfmpoh up uif npsf fmfduspofhbujwf bupn; fmfduspot jo b cpoe cfuxffo bupnt pg uif tbnf fmfnfou bsf opu dpnqvufe. (gpsnbm py. ovncfs = ovncfs pg npsf fmfduspofhbujwf cpoefe bupnt - ovncfs pg mftt fmfduspofhbujwf cpoefe bupnt (f.h. izesphfot)))

40) Oxidation number (7)

Write the oxidation number of the carbon atom C1 in butanenitril. Use one of these examples ( 0, -1, +1, -2, +2, etc.) for your answer.



(Enciphered hint 1: Gps qvsqptft pg dpnqvujoh pyjebujpo tubuft, fmfduspot jo b cpoe cfuxffo bupnt pg ejggfsfou fmfnfout cfmpoh up uif npsf fmfduspofhbujwf bupn; fmfduspot jo b cpoe cfuxffo bupnt pg uif tbnf fmfnfou bsf opu dpnqvufe. (gpsnbm py. ovncfs = ovncfs pg npsf fmfduspofhbujwf cpoefe bupnt - ovncfs pg mftt fmfduspofhbujwf cpoefe bupnt (f.h. izesphfot)))