Organohalides

Question: Name the following alkyl halides:

Question: Name the following alkyl halides:

Name the following alkyl halides:

Name the following alkyl halides:

Draw structures corresponding to the following IUPAC names: (a) 2,3-Dichloro-4-methylhexane.

Draw and name all of the monochlorination products that you might obtain from the radical chlorination of the compounds below. Which of the products is chiral? Are any of the products optically active? 

(a) 2-methylbutane 

(b) Methylcyclopropane

(c) 2,2-dimethylpentane

Predict the product(s) of the following reactions:

A chemist requires a large amount of 1-bromo-2-pentene as starting material for synthesis and decides to carry out an NBS allylic bromination reaction. What is wrong with the following synthesis plan? What side products would form in addition to the desired product?

What product(s) would you expect from the reaction of 1-methyl cyclohexene with NBS? Would you use this reaction as part of a synthesis?

What product(s) would you expect from the reaction of 1,4-hexadiene with NBS? What is the structure of the most stable radical intermediate?

What product would you expect from the reaction of 1-phenyl-2-butene with NBS? Explain.

                                 1-phenyl 2-butene

Rank the compounds in each of the following series in order of increasing oxidation level:

Which of the following compounds have the same oxidation level, and which have different levels?

Question: (S)-3-Methylhexane undergoes radical bromination to yield optically inactive 3-bromo-3-methylhexane as the major product. Is the product chiral? What conclusions can you draw about the radical intermediate?

Question: Assume that you have carried out a radical chlorination reaction on

and have isolated (in low yield) . How many stereoisomers of the product are formed, and in what ratio? Are any of the isomers optically active? (See Problem 10-38.)

How would you carry out the following syntheses?

Question: The syntheses shown here are unlikely to occur as written. What is

wrong with each?

                                                   Reaction 1

                                                      Reaction 2

Question: Why do you suppose it’s not possible to prepare a Grignard reagent from a bromo alcohol such as $\mathbf{4}-\mathbf{bromo}-\mathbf{1}-\mathbf{pentanol}$? Give another example of a molecule that is unlikely to form a Grignard reagent.

Question: Addition of HBr to a double bond with an ether  substituentoccurs regiospecifically to give a product in which the  andare bonded to the same carbon. Draw the two possible carbocation intermediates in this electrophilic addition reaction, and explain usingresonance why the observed product is formed.

Identify the reagents a–c in the following scheme:

Tertiary alkyl halides,${\mathbf{R}}_3\mathbf{CX}$ , undergo spontaneous dissociation to yield a carbocation, ${\mathbf{R}}_3{\mathbf{C}}^{+}$, plus halide ion. Which do you think reacts faster, ${{\text{(CH}}_3\text{)}}_3{\text{CBr or H}}_2{\text{C =CHC(CH}}_3{\text{)}}_2\text{Br}$ ? Explain.

Carboxylic acids (RCOOH; $\mathbf{p}{K}_a$=5) are approximately 1011 times more

acidic than alcohols (ROH; $\mathbf{p}{K}_a$ =16). In other words, a carboxylate ion $\left({{\mathbf{RCO}}_2}^{-}\right)$

is more stable than an alkoxide ion $\left({\mathbf{RO}}^{-}\right)$. Explain, using

resonance.

How might you use a Suzuki–Miyaura reaction to prepare the biaryl compounds below? In each case, show the two potential reaction partners.

The relative rate of radical bromination is 1; 82; 1640 for 1°;2°;3°

hydrogens, respectively. Draw all of the monobrominated products that

you might obtain from the radical bromination of the compounds

below. Calculate the relative percentage of each.

(a) Methylcyclobutane

(b) 3,3-dimethylpentane

(c) 3-methylpentane

Choose the alcohol from each pair below that would react faster with HX to form the corresponding alkyl halide.

Predict the product and provide the entire catalytic cycle for the Suzuki–Miyaura reactions below.