The structures for all of the stereoisomers of 1 , 2 , 3 , 4 , 5 , 6 -hexachlorocyclohexane are to be written, with meso forms and pair of enantiomers labeled. Also, the stereoisomer that undergoes slow E2 reactions is to be identified along with the reason is to be explained. Concept Introduction: Stereoisomers are isomers that have the same atoms but are arranged differently, that is, the same molecular formula but different structural formulae. Enantiomers are the stereoisomers having non-superimposable mirror images of each other. Enantiomers have same physical and chemical properties. A meso compound is a molecule that has a mirror image, and also has a plane of symmetry. E2 elimination reaction is one of the elimination processes which proceeds via one step mechanism, resulting in two products, also called bimolecular reaction. The order of the reaction is 2 and the rate depends on both the substrate and the base. In E2 elimination reaction an alkene is formed. In E2 reactions the two elimination reactions should be anti periplanar to each other.

Question

Q2: Ranking Acidity a) Rank the labeled protons in the following molecule in order of increasing pKa. Briefly explain the ranking. Use Table 2.2 as reference. Ha Нь HC H-N Ha OHe b) Atenolol is a drug used to treat high blood pressure. Which of the indicated N-H bonds is more acidic? Explain. (Hint: use resonance structures to help) Name the functional groups on atenolol. H H-N atenolol Ν H-N OH Н

Answer 1

Question

Chapter FRP, Problem 37P

Interpretation Introduction

Interpretation:

The structures for all of the stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane are to be written, with meso forms and pair of enantiomers labeled. Also, the stereoisomer that undergoes slow E2 reactions is to be identified along with the reason is to be explained.

Concept Introduction:

Stereoisomers are isomers that have the same atoms but are arranged differently, that is, the same molecular formula but different structural formulae.

Enantiomers are the stereoisomers having non-superimposable mirror images of each other. Enantiomers have same physical and chemical properties.

A meso compound is a molecule that has a mirror image, and also has a plane of symmetry.

E2 elimination reaction is one of the elimination processes which proceeds via one step mechanism, resulting in two products, also called bimolecular reaction. The order of the reaction is 2 and the rate depends on both the substrate and the base. In E2 elimination reaction an alkene is formed. In E2 reactions the two elimination reactions should be anti periplanar to each other.

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Q2: Ranking Acidity a) Rank the labeled protons in the following molecule in order of increasing pKa. Briefly explain the ranking. Use Table 2.2 as reference. Ha Нь HC H-N Ha OHe b) Atenolol is a drug used to treat high blood pressure. Which of the indicated N-H bonds is more acidic? Explain. (Hint: use resonance structures to help) Name the functional groups on atenolol. H H-N atenolol Ν H-N OH Н

Answer d, e, and f

If the rotational constant of a molecule is B = 120 cm-1, it can be stated that the transition from 2←1:a) gives rise to a line at 120 cm-1b) is a forbidden transitionc) gives rise to a line at 240 cm-1d) gives rise to a line at 480 cm-1