When it is treated with sodium ethoxide in deuterated ethanol (C2H5OD), cyclopentadiene exchanges all of its hydrogens for deuterium. Draw a structure for the intermediate in this reaction with all protons (no deuterons).

Suppose you are told that each reaction is a substitution reaction but are not told the mechanism. Describe how you could conclude from the structure of the haloalkane, the nucleophile, and the solvent that each reaction is an SN2 reaction.

Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle

An unknown compound is treated with HBr in the dark. The product of this reaction is reacted with potassium t- butoxide. The product of reaction 2 is treated with HBr and peroxide. In reaction 4 the product of reaction 3 is treated with lithium acetylenide (C2H"). The product of reaction4 is reduced with hydrogen using platinum as a catalyst. This final product was determined to be n-pentylcyclopentane. What is the name of the original unknown compound? ABC T T T Arial 3 (12pt) Path: p Words:0

Draw the structure of the starting material needed to make 2-methylhept-3-yne using sodium amide in liquid ammonia, followed by 1-bromopropane. The starting hydrocarbon must have no more than five carbons 1) NaNH2, NH3() NaBr + 2) CHзCH2CH2Br

What are the reagents used to convert 2-butyne to C4H8? What are the products when that C4H8 is mixed with OsO4, and H2O (the formula will be C4H10O2 racemic)? What is the product when C4H8 is mixed with RCO3H, and H2O (the formula will be C4H10O2 meso)?

n-Pentanol (CH3CH2CH2CH2CH2OH) and 2-methylbutan-2-ol (CH3CH2C(CH3)2OH) are converted to their corresponding alkyl chorides on being reacted with hydrogen chloride. (a) Write out an equation for each reaction (b) Assign each the appropriate symbol (SN1 or SN2) (c) Write a suitable mechanism for each reaction