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Chapter 3: Q48P (page 190)

Question: Convert each Newman projection to the equivalent line-angle formula, and assign the IUPAC name.

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Step by step solution

01

IUPAC nomenclature

A systematic way of naming organic compounds based on their chemical composition and structure is given by IUPAC nomenclature.

02

Newman projection

Newman projections are often used in drawing conformations. In Newman鈥檚 projection, one views the bond end along the axis of connection.The front carbon is represented by the intersection of bonds, while the rear carbon appears as a circle.

03

 Step 3: Converting Newman projection into a line-angle formula and assigning their IUPAC names

In order to show the connectivity of carbon atoms more precisely, Newman projections are converted into a bond-line formula.

a.

b.

c.

d.

e.

f.

g.

h.

i

j

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Most popular questions from this chapter

List each set of compounds in order of increasing boiling point.

(a) hexane, octane, and decane

(b) octane, (CH3)3C-C(CH3)3, and CH3CH2C(CH3)2CH2CH2CH3

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentanealong theC2鈭�C3.PlaceC2in front, represented by three bonds coming together in a Y shape, andC3in back, represented by a circle with three bonds pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and ethyl group on the back carbon. Begin your graph at 00thedihedral angle and begin to turn the front carbon. Show the Newman projection and the approximate energy at each600of rotation. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).

Question: Using the general formula for alkanes

(a) Predict the molecular formula of theC27straight chain alkane.

(b) Predict the molecular formula of the alkanes containing 42 carbon atom with extensive branching.

Provide IUPAC names for the following compounds.

(a)


(b)

(c)

(d)

(e)

( f)

Question: Conformational studies on ethane-1,2-diol (HOCH2 -CH2OHhave shown the most stable conformation about the central C-Cbond to be the gauche conformation, which is 9.6 KJ/mol (2.3 kcal/mol)more stable than the anti-conformation. Draw Newman projections of these conformers, and explain this curious result.
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