Show:
Synthesis
Radicals
S & E Families
100
Show the arrow pushing mechanism for the radical bromination of butane

One product, bromine on the second carbon

100

What is the substitution product of tertbutyl bromide and H2O?

Alcohol on the tertiary carbon

200

Show the product of the addition of Hg(OAC)2, H2O, and NaBH4 to but-1-ene

oxymercuration demurcuration adds an alcohol to the most substituted carbon

300

Show the arrow pushing mechanism for the elimination of (1R,2S) 2bromo 1 methyl cyclohexane  

NEED TO DO THIS

300
Show all products for the reaction between cis 1 methyl 2 bromo cyclohexane and water. Consider drawing the arrow mechanism as a safety net/reminder. Circle your major elimination product. 

1. substitution products: OH on carbon 2 before rearrangement. OH on carbon 1 after a hydride shift

2. elimination products: 2, you could take the adjacent hydrogen from the carbon with the methyl or the one without it. The major is the one with the double bond between the methyl and carbon

400

Draw the arrow pushing mechanism for how 2bromo 3,3 dimethylpentane becomes 3,3dimethyl pent-1-ene

Must do E2 with a bulky base

400

Show all products for the radical chlorination of methyl cyclohexane. No arrow pushing needed

Should have 5 products


400

Show all possible products for the reaction between NaOH and heat and this reactant: (sorry I can't insert pictures)

a bromine on a wedge on carbon 1

a methyl on a wedge on carbon 2

and a methyl on a dash on carbon 6

you must consider antiperiplanar when doing E2 on a cyclohexane.

this means they must be trans diaxial. which means, you can only take trans Hydrogens, aka only the one on C2.

So you will have your one SN2 product with inversion of stereochemistry, and one elimination product

500

Draw a synthesis (no arrows) that does not involve substitution to show how propane becomes 2-hydroxy propane (propane with an alcohol on carbon 2). 

*hint 1* cumulative

*hint 2* check ch 8 

1. add leaving group through Br2/Cl2 radical

2. eliminate using E1/E2

3. Use either acid-catalyzed hydration or oxymercuration demurcuration 

500

Show the allylic bromination product(s) for but-1-ene 

products should be:

3-bromo but-1-ene

and

1-bromo but-2-ene

500

Show all possible products for the reaction of 1-chloro-1-methyl cyclohexane and warm CH3CH2CH2OH

Elimination products possible: 2. One from the hydrogen in the ring, one from the CH3 group

Only 1 substitution product possible (in my perspective) but will take a hydride shift into the ring as accurate