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Chapter 8: Q.6 (page 303)

Which alkene in each pair is more stable?

a.

b.

c.

Short Answer

Expert verified

a. In the case of a., the stable structure is:

b. In the case of b., the stable structure is:

c. In the case of c., the stable structure is:

Step by step solution

01

Identification of the double-bonded carbons

The double bonds are identified first and marked as blue.

Representation of the double bond in the structure

02

For pair (a), both the structures are disubstituted

For pair (a), both the structures are disubstituted

Pair a

In the case of (b), the first structure is trisubstituted, whereas the second one is disubstituted.

Pair b

For (c), both are disubstituted.

Pair c

03

Stability based on trans-orientation and electron-donating groups

Stability on the double bond depends upon two factors:

  • When the high priority groups are in a trans orientation, there will be no repulsion among the groups, and as a result, the alkene gets stable.
  • The introduction of the alkyl groups donates electrons through the +I effect. So when more alkyl groups are added, the +I effect too increases, and stability increases too.

For pair (a), the second structure is more stable due to the presence of two alkyl groups which through its +I effect imparts stability to the double bond.

More stable structure in pair a

For pair (b), the second structure is more stable due to the presence of three alkyl groups which through its +I effect imparts stability to the double bond. The structure is trisubstituted, unlike the first pair, which is disubstituted.

More stable structure in pair b

For pair (c), the second structure is more stable due to its trans orientation, which imparts less repulsion among the alkyl groups.

More stable structure in pair c

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Most popular questions from this chapter

Consider an E2 reaction between CH3CH2Brand KOC(CH3)3. What effect does each of the following changes have on the rate of elimination? (a) The base is changed to KOH. (b) The alkylhalide is changed to CH3CH2Cl.

Classify each alkene in the following vitamins by the number of carbon substituents bonded to the double bond.

a.

b.

For which reaction mechanisms鈥�SN1,SN2,E1, or E2鈥攁re each of the following statements true? A statement may be true for one or more mechanisms.

a. The mechanism involves carbocation intermediates.

b. The mechanism has two steps.

c. The reaction rate increases with better leaving groups.

d. The reaction rate increases when the solvent is changed from CH3OHto localid="1648646954099" (CH3)2SO.

e. The reaction rate depends on the concentration of the alkyl halide only.

f. The mechanism is concerted.

g. The reaction of localid="1648646960420" CH3CH2Brwith NaOH occurs by this mechanism.

h. Racemization at a stereogenic center occurs.

i. Tertiary (3掳) alkyl halides react faster than 2掳 or 1掳 alkyl halides.

j. The reaction follows a second-order rate equation.

Which mechanism, E1 or E2, will occur in each reaction?

a.

b.

c.

d.

Label the 伪and 尾carbons in each alkyl halide. Draw all possible elimination products formed when each alkyl halide is treated with role="math" localid="1648539176246" K+-OC(CH3)3.

a.

b.

c.
See all solutions

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