Synthesis
One product, bromine on the second carbon
What is the substitution product of tertbutyl bromide and H2O?
Alcohol on the tertiary carbon
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
Show the arrow pushing mechanism for the elimination of (1R,2S) 2bromo 1 methyl cyclohexane
NEED TO DO THIS
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
Draw the arrow pushing mechanism for how 2bromo 3,3 dimethylpentane becomes 3,3dimethyl pent-1-ene
Must do E2 with a bulky base
Show all products for the radical chlorination of methyl cyclohexane. No arrow pushing needed
Should have 5 products
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
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
Show the allylic bromination product(s) for but-1-ene
products should be:
3-bromo but-1-ene
and
1-bromo but-2-ene
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