CHE 128B

HOMEWORK-2
Ex 4.1

Each of the following compounds is characterized by a 1H NMR spectrum that consists of

two peaks, both singlets, having the chemical shifts indicated. Identify each compound.
a. C6H8; 2.7 ppm (4H) and 5.6 ppm (4H)
b. C6H12O; 1.1 ppm (9H) and 2.1 ppm (3H)

Ex 4.2

Deduce the structure of each of the following compounds on the basis of their 1H NMR
spectra and molecular formulas
C6H14 - 0.8 ppm (doublet, 12H)
- 1.4 ppm (heptet, 2H)

Ex 5.1

Write structural formulas for each of the following compounds. Specify which compounds
qualify as organometallic compounds.
a. 2-Phenylethylmagnesium iodide
b. Ethoxymagnesium chloride

Ex 5.2

Suggest appropriate methods for preparing each of the following compounds from the
starting material of your choice.
CH3CH2CCMgI

Ex 5.3

Write the structure of the principal organic product of each of the following reactions:
a. 2-Iodopropane with magnesium in diethyl ether
b. Product of part (a) with formaldehyde in ether, followed by dilute acid

Ex 5.4

Using 1-bromobutane and any necessary organic or inorganic reagents, suggest efficient
syntheses of each of the following alcohols:
a. 3-Methyl-3-heptanol
b. 2-Hexanol

Ex 5.5

Predict the principal organic product of each of the following reactions

a.
b.

Ex 6.1

Write chemical equations, showing all necessary reagents, for the preparation of 1-butanol
by each of the following methods:
a. Use of a Grignard reagent
b. Hydrogenation of an aldehyde
c. Reduction with sodium borohydride

Ex 6.2

Write chemical equations, showing all necessary reagents, for the preparation of tert-butyl
alcohol by reaction of a Grignard reagent with a ketone.

Ex 6.3

Which of the isomeric C5H12O alcohols can be prepared by lithium aluminum hydride
reduction of carboxylic acid.

Ex 6.4

Evaluate the feasibility of the route

as a method for preparing 1-Butanol from butane

Ex 6.5

Write equations showing how 1-phenylethanol C6H5CH(OH)CH3 could be prepared from

each of the following starting materials.
a. Bromobenzene
b. Benzene

Ex 7.1

Write the structures of all the constitutionally isomeric ethers of molecular formula C5H12O and give
an acceptable name for each.

Ex 7.2

Predict the principal organic product of each of the following reactions. Specify stereochemistry
where appropriate

a.

Ex 7.3

b.
Select reaction conditions that would allow you to carry out the following stereospecific
transformations

Ex 8.1

(a) Write structural formulas and provide IUPAC names for all the isomeric aldehydes and ketones
that have the molecular formula C5H10O. Include stereoisomers.
(b) Which of the isomers in part (a) yield chiral alcohols on reaction with sodium borohydride?

Ex 8.2

Predict the product of the reaction of propanal with each of the following
a. Sodium borohydride
b. Phenyllithium, followed by dilute acid

c. Aniline (C6H5NH2)
Ex 8.3

Hydride reduction (with LiAlH4 or NaBH4) of the following ketones has been reported in the
chemical literature and gives a mixture of two diastereomeric alcohols in each case.
Give the structures or build molecular models of both alcohol products for each ketone.
a.

b. (S)-3-Phenyl-2-butanone
Ex 8.4

Each of the following reactions has been reported in the chemical literature and gives a single
organic product in good yield. What is the principal product in each reaction?
a.

b.

Ex. 9.1

(a) Write structural formulas or build molecular models for all the noncyclic aldehydes and ketones
of molecular formula C4H6O.
(b) Are any of these compounds stereoisomeric?

Ex. 9.2

In each of the following pairs of compounds, choose the one that has the greater enol content, and
write the structure of its enol form:
a.

b.

9.3

Give the structure of the expected organic product in the reaction of 3-phenylpropanal with each of
the following:
(a) Chlorine in acetic acid
(b) Sodium hydroxide in ethanol, 70C