b) Optical isomers can often be formed during these reactions. For products A-H. indicate how many different optical isomers you expect to form for each from these reactions (you do not have to indicate whether they are diastereomers/enantiomers). c) In the preparation of substance D by ozonolysis, the second step is necessary-treatment of the reaction mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which would probably explode when isolated. What is the structure of substance V? X 1: ozone V e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III - PhSCI in diethyl ether; IV-Selectfluor in methanol. M N PhSNa O EtOH H* EtOH EtONa TSCI Pyridin E- F T₂, Pd/C G- mCPBA H₂SO4 10 %, H₂O 1: BH3 H- 2: H₂O₂ X Br₂ cyclohexane HCI A B HBr warmth, benzoylperoxid 1: ozone 2: Zn, ACOH Mg THF C D L 1020 K NaOH

7) CH₂CH₂Br (hint: few necessary reagents: Mg, PBr3, D₂O) CH₂CH₂CH₂CH₂D

Draw the structure of the expected organic produect formed in the following reactions including correct relative stereochemistry; if the reaction is racemic indicate this by either drawing both enantiomers or drawing one and writing racemic. Assume all reagent are present in excess unless otherwise noted. If no reaction occurs, state "No Reaction".

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f) Alkene X can be decomposed with hydrogen peroxide catalyzed by sodium tungstate to substance Q. This can be further degraded by iodoform reaction to substance R. Give the structures of substances Q and R. Xx S Na₂WO4 H₂O2 Q (C9H1603) 1: NaOH, 1₂ 2: H+ P₂O5 teplo - CHI3 R (C8H1404) P₂O5 teplo T g) The preparation of substance Q from substance X using hydrogen peroxide is a redox reaction. Identify the reductant and oxidant in this reaction, write the formal oxidation number to the atoms where it changes during the reaction and calculate the reaction. h) Substances Q and R undergo a reaction with phosphorous oxide under heating to form various products T and S. Determine the structure of substances T and S if you know their H NMR : 1H NMR (S): 2.2 (t, 2H); 1.8 (t, 2H); 1.3 (s, 6H). 1H NMR (T): 4.6 (d, 1H); 4.3 (d, 1H); 2.2 (t, 2H); 1.5 (t, 2H); 1.3 (s, 6H).

Provide the systematic name for each of the following isomeric esters with the chemical formula C-H₁2O₂. (Be sure to indicate double bond stereochemistry using (E)/(Z) notation. Indicate stereochemistry in rings with the terms cis or trans. It is not necessary to use italics in writing compound names.) ball & stick - + labels ball & stick- + labels ball & stick + labels 12

see these instructions. Consider stereochemistry and enter either enantiomer (but not both) if a racemic mixture of products forms. If a mixture of two diastereomers is expected, enter either (but not both). 1. MgCl 2. H₂O

Consider the sequence of reactions below. In this sequence of reactions, an unsaturated ketone is treated with a Gilman reagent, followed by treatment with an aqueous base. The base allows a rapid equilibration to take place, producing the more stable stereoisomer of the product. 1. Et,CuLi 2. Equilibration with base For this process: show both stereoisomeric products, explain which is more stable, and explain why aqueous base allows equilibration between the stereoisomers.

Optical active compound 1-chloro-3-methylcyclopentane was reacting withpotassium t-butoxide in t-butanol. Two alkene products were obtained. Themain product was optically active, and the secondary product was notoptically active. What are the two products?

iii.Draw the structures of the major organic product(s) or condition(s) denoted by A to E in the following reactions. Show stereochemistry of products, if any. OH Br base (e.g. NaH or NaOH) C