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Predict the products formed by sodium hydroxide-promoted dehydrohalogenation of the following compounds. In each case, predict which will be the major product.
(a) 1-bromobutane
(b) 2-chlorobutane
(c) 3-bromopentane
(d) cis-1-bromo-2-methylcyclohexane
(e) trans-1-bromo-2methylcyclohexane
Show that the (S,S) enantiomer of this (R,R) diastereomer of 1-bromo-1,2-diphenylpropane also undergoes E2 elimination to give the cis diastereomer of the product. (We do not expect these achiral reagents to distinguish between enantiomers.)
Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2。 alkyl halide) with sodium ethoxide.
The following names are all incorrect. Draw the structure represented by the incorrect name (or a consistent structure if the name is ambiguous), and give your drawing the correct name.
(a) Cis-dimethylpent-2-ene
(b) 3-vinylhex-4-ene
(c) 2-methylcyclopentene
(d) 6-chlorocyclohexadiene
(e) 2,5-dimethylcyclohexene
(f) Cis-2,5-dibromo-3-ethylpent-2-ene
Draw five more compounds of formula C4H6NOCl.
Determine the number of elements of unsaturation in the molecular formula C3H4. Give all three possible structures having this formula. Remember that
a double bond = one element of unsaturation
a ring = one element of unsaturation
a triple bond = two elements of unsaturation
Give five examples of structures with this formula (C5H10). At least one should contain a ring, and at least one should contain a double bond.

c) Explain using structures why trans-2-Butene (a disubstituted alkene) is more stable than cis-2-butene (another disubstituted alkene)?


a) Draw all the three staggered conformations of butane when viewed along the C2-C3 bond, using Newman’s projection. Explain clearly which of the conformations you have drawn is the most stable.


What is the iupac name of CH(CH3)2ONa
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