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(a) What ratio of primary/secondary/tertiary products can statistically be expected in the high temperature chlorination of methyl butane? Assume that the reaction rate of the substitution is equal for all C-H bonds. 

(b) Which of the following alcohols:pentan-1-ol, pentan-2-ol and 2-methyl-butan-2-ol react with the following reagents listed below? 

 1) cold, concentrated sulphuric acid; 2) CrO3 / H2SO4; 3) ZnCl2 /HCl;4) I2 /NaOH 

(c) Which of the following aldohexose structures are: 1) enantiomer pairs, 2) diastereomer pairs? 

(d) Two hydrocarbon compounds of the same molecular formula, C4H8, easily react with hydrogen in the presence of a platinum catalyst. During ozonolysis only ethanal (acetaldehyde) is formed in both cases. The 1H-NMR spectra of the two compounds show two types of protons in a ratio of 3 to 1. Draw the structures of the described compounds. 

(e) Select the components of the group listed below that can be obtained during complete hydrolysis of lecithin (a phospholipid): serine, phosphoric acid, sphingosine, choline, glycerol, myo-inositol, phosphatidic acid and fatty acids). 

(f) Which of the following carboxylic acid can be formed in the tricarboxylic acid cycle (Krebs' citric acid cycle): maleic acid (cis-butenedioic acid), mandelic acid (a-hydroxy-phenylethanoic acid), malic acid (2-hydroxy-butanedioic acid), tricarb-allylic acid (propane-1,2,3-tricarboxylic acid), oxalacetic acid (2-oxo-butanedioic acid), keto-glutaric acid (2-oxo-pentanedioic acid), fumaric acid (trans-butenedioic acid) and acetoacetic acid (3-oxo-butanoic acid). 

(g) To which structures is the nicotinamide moiety (part) of NAD+ converted during the uptake of hydrogen to form NADH (A, B or C)? 

1 Answer

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(a) The ratio of primary, secondary and tertiary products will be 9 : 2 : 1. 

(b) 1-Pentanol reacts with 1) cold conc. sulphuric acid (elimination) and with2) CrO3/H2SO4 (oxidation).2-Pentanol reacts with 1)under elimination,with 2) under oxidation, with 3) under reduction and with 4) (haloform oxidation). 2-Methyl-2-butanol reacts with 1) under elimination and with 3) under reduction. 

(c) a/c and b/d are enantiomers, a/b,a/d,b/c and c/d are diastereomers. 

(e) Glycerol,choline,phosphoric acid and fatty acids can be found during complete hydrolysis of lecithin. 

(f) maleic acid,oxalacetic acid,ketoglutaric acid, fumaric acid 

(g) c) is correct since the NAD+ is converted into NADH/H

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