Organohalides

Give IUPAC names for the following alkyl halide (a):

(a)

Give IUPAC names for the following alkyl halide (b):

(b)

Give IUPAC names for the following alkyl halide (c):

Give IUPAC names for the following alkyl halide (d):

Give IUPAC names for the following alkyl halide (e):

Give IUPAC names for the following alkyl halide (f):

Draw structures corresponding to the following IUPAC names: (a) 2-Chloro-3,3-dimethylhexane.

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

Draw structures corresponding to the following IUPAC names: (c) 3-Bromo-3-ethylpentane.

Draw structures corresponding to the following IUPAC names: (d) 1,1-Dibromo-4-isopropylcyclohexane.

Draw structures corresponding to the following IUPAC names: (e) 4-sec-Butyl-2-chlorononane.

Draw structures corresponding to the following IUPAC names: (f) 1,1-Dibromo-4-tert-butylcyclohexane.

Draw and name all monochloro products you would expect to obtain from radical chlorination of 2-methylpentane. Which, if any, are chiral?

Taking the relative reactivities of 1°, 2°, and 3° hydrogen atoms into account, what product(s) would you expect to obtain from monochlorination of 2-methylbutane? What would the approximate percentage of each product be? (Don’t forget to take into account the number of each kind of hydrogen.)

Draw three resonance forms for the cyclohexadienyl radical.

Cyclohexadienyl radical

The major product of the reaction of methylenecyclohexane with N-bromosuccinimide is 1-(bromomethyl)cyclohexene. Explain.

What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.

What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.

How would you prepare the following alkyl halides from the corresponding alcohols?

How would you prepare the following alkyl halides from the corresponding alcohols?

How would you prepare the following alkyl halides from the corresponding alcohols?

Question: How would you prepare the following alkyl halides from the corresponding alcohols?

Question: How strong a base would you expect a Grignard reagent to be? Look at Table 9-1 on page 276, and predict whether the following reactions will occur as written. (The ${\mathrm{pK}}_{\mathrm{a}}$of ${\mathrm{NH}}_3$is 35.)

Question: How strong a base would you expect a Grignard reagent to be? Look at Table 9-1 on page 276, and predict whether the following reactions will occur as written. (The ${\mathrm{pK}}_{\mathrm{a}}$ of ${\mathrm{NH}}_3$ is 35.)

(b) 

Question: How might you replace a halogen substituent by a deuterium atom if you wanted to prepare a deuterated compound?

Alkyl halides can be reduced to alkanes by a radical reaction with tributyltinhydride, ${\left({\mathrm{C}}_4{\mathrm{H}}_9\right)}_3\mathrm{SnH}$ in the presence of light (hv). Propose a radical chain mechanism by which the reaction might occur. The initiation step is the light-induced homolytic cleavage of the Sn-H bond to yield a tributyltin radical.

$\mathrm{R}-\mathrm{X}+{\left({\mathrm{C}}_4{\mathrm{H}}_9\right)}_3\mathrm{SnH}\stackrel{\mathrm{hv}}{\to }\mathrm{R}-\mathrm{H}+{\left({\mathrm{C}}_4{\mathrm{H}}_9\right)}_3\mathrm{SnX}$

Draw structures corresponding to the following IUPAC names: (b) 4-Bromo-4-ethyl-2-methylhexane.

Draw structures corresponding to the following IUPAC names: (c) 3-Iodo-2,2,4,4-tetramethylpentane

Draw structures corresponding to the following IUPAC names: (d) cis-1-Bromo-2-ethylcyclopentane

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (a) Chlorocyclopentane.

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (b) Methylcyclopentane.

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (c) 3-Bromocyclopentene.

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (d) Cyclopentanol.

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (e) Cyclopentylcyclopentane.

How would you prepare the following compounds, starting with cyclopentene and any other reagents needed? (f) 1,3-Cyclopentadiene.

Tell whether each of the following reactions is an oxidation, a reduction, or neither:

Tell whether each of the following reactions is an oxidation, a reduction, or neither:

Tell whether each of the following reactions is an oxidation, a reduction, or neither:

Sort the radicals below from most stable to least stable.

Sort the radicals below from most stable to least stable.

Sort the radicals below from most stable to least stable.

Alkylbenzenes such as toluene (methylbenzene) react with NBS to give

products in which bromine substitution has occurred next to the aromatic ring (the benzylic position). Explain, based on the bond dissociation energies in Table 6-3 on page 170.

Draw resonance structures for the benzyl radical, the intermediate produced in the NBS bromination reaction of toluene (Problem 10-35).

Draw resonance structures for the following species:

Draw resonance structures for the following species:

Draw resonance structures for the following species:

Draw the electron-pushing mechanism for the propagation steps of the allylic bromination reactions below. You may omit NBS in your mechanism, and use Br∙ and Br₂.

(b)

Draw the electron-pushing mechanism for the propagation steps of the allylic bromination reactions below. You may omit NBS in your mechanism, and use Br∙ and 

(c)

In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.

Question: Name the following alkyl halides: