Chapter 9, Problem 65P

6. Draw a tetrahedral representation of (R)-3-chloropent-1-ene.

0 || CH,-O-C-(CH2)2 – CH3 O || CH-O - C - (CH2), – (CH = CH – CH2)2 – (CH2)3 – CH3 O || CH,- O-C-(CH2)8 – CH3 - 3 KOH

Methyl isocyanate, CH3 -N= C = O, is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 people were exposed to its vapors, and over 2000 of these people died. Q.) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet

4. A student was asked to prepare an alkene X in high yield using any alcohol as starting material CH3 CH,-C -CH=CH, CH3 X He chose 3, 3-dimethylbutan-2-ol (XI) and carried out a dehydration reaction. He was however horrified to note that the only alkene obtained was XII. CH3 OH CH3 CH;-C=C-CH3 conc. H,SO4 CH-CH3 heat CH3 CH3 XI XII i) Explain what went wrong here, and why X could not be formed from 3, 3-dimethylbutan-2-ol. Use structures to help support your answer. ii) Give an equation to show a much better method for preparing X in high yield. 5. Analyze the following structure and write one combination for Grignard reagent and a carbonyl that would give rise to it. CH,-CH,-OH

Complete the following reaction by drawing a structural formula for the product. CH,CH, (1) NABH4 ? (2) H30* • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.

Give the proper IUPAC name for the molecule shown as a Fischer projection. Make sure to include the correct (R) or (S) designation where appropriate. CH3 H. Br Br- H ČH;CH3 The name of the molecule is: O (3S,4S)-3,4-dibromopentane O (3S,4R)-3,4-dibromopentane O (2R,3S)-2,3-dibromopentane O (2S,3S)-2,3-dibromopentane

Name the heterocyclic substituent found in the molecule shown according to the general type of nitrogen-containing ring to which it belongs. NH2 O- O=P-0-CH2 `N' O. O- нн H ОН ОН

1. Identify (draw the structure) of the missing reactant, reagent, or major product required to complete the following transformations. If the product gives two enantiomers, you only need to give one. Cl2 H20 OH H2, Pd МСРВА 1.Hg(OAc H,O 2.NaBH, OH

Draw all stereoisomers formed in the reaction shown. Use wedges and dashes for tetrahedral stereogenic centers, if applicable. NaCN HC1 Click and drag to start drawing a structure. A E *0