Question

[01] Give all three termination steps (using structures) for a radical chain reaction monochlorination (Clh/hv) of cyclopropane to give chlorocyclopropane 1. 2. [01] a. Give the resulting structure from the following electron flow. b. Give the curved arrows on structure at left to indicate the electron flow in going to the resonance structure on the right. Be precise. 3. [O1] Give the structure of the major product for the following reaction as well as the two allylic resonance structures from which it is derived H-Cl (1 mole) A, 2 days 4. [01] a. Give the product of this intramolecular Diels-Alder reaction. b. The ring on the right is form by a Diels-Alder reaction. Give the two reactants dienophile S-ACP . [1.5] Give the mechanism for the following reaction (2 steps). H-CN O1-cyano-1-cyclobutanol

Answer 1

hv 2 Cl . initiation 1. [01] Give all three termination steps (using structures) for a radical chain reaction monochlorination (Clh/hv) of cyclopropane to give chlorocyclopropanc propagation 2. [01] a. Give the resulting structure from the following clectron flow. b. Give the curved arrows on structure at left to indicate the electron in going to the resonance structure on the right. Be precise 3. [01] Give the structure of the major product for the following reaction as well as the two allylic resonance structures from which it is derive Δ. 2 days product 4. [01] a. Give the product of this intramolecular Dicls-Alder reaction. b. The ring on the right is form by a Diels-Alder reaction. Give two reactants. S-ACP Heat [1.5] Give the mechanism for the following reaction (2 steps). H-CN NC CN

6. [0.5] A representation of polyacrylonitrile, used to make acrylic fabrics, is shown. What is the monomer's structure? CN CN CN 3. [04] Give the structure of the major product for each of the following reactions a. HO он LiAIH4 OH then H+/H2O Br hv C. CH,CH2MgBr он then IH /H,0

d. HO NaBH4 OCH CH,OH OCH3 но NaBD4 CH3OH OCH3 он OH DMSO(COCI, low temp, then Et,N or PCC /CH2Cl2 он H2CrO4 HO h. H-Br peroxides f the following syntheses

4. [03] Give the structure of the final major product for each of the following syntheses. a. 1. CH,MgBr in Et20, then H+ 2. H2CrO4 4 3. CH CH2MgBr in El20, then H он H 1. EtMgBr но 2. acetone, then H/H20 3. H2/ Lindlar's catalyst c. 1. TBSCI, imidiazol он H2. isopropylmagnesium bromide TBSO then H+/H20 3. Bu4N+F 5. [02] Give the structures of three (3) different combinations of Grignard reagents and aldehydes or ketones that when followed by H'/H,0 would yield the following alcohol. но MgBr Ph