These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.
Give the names of the following organohalides:
Draw the structures of the following compounds:
A – 2-Chloro-3,3-dimethylpentane
B – 1,1-Dichloro-4-isopropylcyclohexane
C – 3-bromo-3-ethylhexane
A – 5-ethyl-4-iodo-3methyl-octane
B – 1-bromo-2,3,4-trimethyl-pentane
C – 4-bromo-5-chloro-2-methyl-heptane
Predict the mono-substituted halogenated product(s) of chlorine gas reacting with 2-methylbutane.
Predict the relative amount of each mono-brominated product when 3-methylpentane is reacted with Br2. Consider 1°, 2°, 3° hydrogen.
The following reaction shows the major product. Explain why this would be the final product and why the 2° bromo product is not the major product.
Predict the products of the following reactions:
The product (A) is a 1° halogen which is more predominant product even though the (B) had a better transition state with a 2° radical. The 1° radical intermediate is not as sterically hindered.
Predict the alcohol required for the synthesis of the following halides:
How strong of a base would you expect ethyl Grignard to be? Would the following reactions be able to take place?
How would you make a deuterated compound from an alkyl halide?
Because hydrocarbons like ethane are very weak acids (pKa = 50), then the corresponding carbanion (CH3CH2-) is expected to be a strong base. Both reactions will occur.
By first making a Grignard and then exposing it to heavy water.
In each case state whether the reaction is an oxidation or reduction of the organic compound.
A – Reduction
B – Oxidation