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Chapter 3: Q49 (page 190)

Question: Draw Newman projections along the C3-C4bond to show the most stable and least stable conformations of 3 ethyl-2,4demethylheptane.

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01

Newman projection

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

02

Using Newman projections to draw the most stable conformer

The two bulky groups (propyl and isopropyl) are anti-periplanar in most stable conformations, while in the least stable, the two bulky groups (propyl and isopropyl) are syn-periplanar.

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Most popular questions from this chapter

Use a Newman projection about the indicated bond to draw the most stable conformer for each compound.

(a)3-methylpentane  about  the C2−C3  bond

(b)3,3-dimethylhexane  about  the C3−C4  bond

Write structures for a homologous series of alkyl chloridesR-Cl having from one to six carbons.

Draw the structures of the following compounds.

(a) 4-(1,1-dimethylethyl)nonane

(b) 5-(1,2,2-trimethylpropyl)decane

(c) 3,3-diethyl-4-(2,2-dimethylpropyl)nonane

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.

Without looking at the structures, give molecular formulas for the compounds in Problem 3-8 (a) and (b). Use the names of the groups to determine the number of carbon atoms; then use the (2n+2) rule.
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