Give the major product of the monobromination of n-butane (or butane) in the presence of light or heat. Propose a mechanism for this reaction and name the product. Provide 2 reactions in the termination step.

Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R OH 1. HC=C: Na* 2. H30* R2 Rí `R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. H H3C H CH3

Benzene can be hydroxylated by treating it with hydrogen peroxide and a strong acid such as trifluoromethanesulfonic acid (TfOH). Propose amechanism for this reaction

Ph3P-CHCH3 H₂C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. CH3 00 + The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an SN2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene X m CH3 The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C=C bond is precisely where the C=O bond was in the reactant and no isomers (other than E/Z isomers)…

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the major product. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. ● 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Ⓡ n [ ]#

Provide the structure of the major organic product of following ring opening reaction. CH;ONa CH;OH

In this chapter, we studied the mechanism of the acid-catalyzed hydration of an alkene. The reverse of this reaction is the acid-catalyzed dehydration of an alcohol. OH H,SO, CH,-CH-CH, CH-CH=CH, + H,O 2-Propanol (Isopropyl alcohol) Propene Propose a mechanism for the acid-catalyzed dehydration of 2-propanol to propene.

Just to reiterate, the question is to draw out all possible alkene reactants that will result in the shown product.

NAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of hydrogenation. Give reasons for your choice.

Give the major organic product(s) of the following reactions for a)