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Chapter 8: Q.7 (page 303)

Several factors can affect alkene stability. Explain why alkene A is more stable than alkene B even though both contain disubstituted carbon-carbon double bonds.

Short Answer

Expert verified

Alkene A is more stable since the double bond is present in a 6-membered ring where the alkene suffers less angular strain.

Step by step solution

01

Alkene

Alkene is one of the unsaturated hydrocarbons in which double bonds are present. The general formula to represent alkenes is CnH2n.

Where n is the carbon count.

02

Classification based on substitution

Both the structures are disubstituted and are marked as black, but the double bond is marked as blue.

Representation of the substituents across the double bond

03

Stability based on angle strain

Angle strain is caused when the bond angles deviate from their ideal value. The observed strain energy is found to be much higher in a four-membered ring as compared to a six-membered ring.

Hence, alkene A is more stable since the double bond is present in a six-membered ring where the alkene suffers less angular strain.

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Most popular questions from this chapter

Consider the following E2 reaction.

a. Draw the by-products of the reaction and use curved arrows to show the movement of

electrons.

b. What happens to the reaction rate with each of the following changes? [1] The solvent is changed to DMF. [2] The concentration of -OC(CH3)3is decreased. [3] The base is changed to localid="1648628375469" OH-. [4] The halide is changed to localid="1648628387551" CH3CH2CH2CH2CH(Br)CH3[5] The leaving group is changed to localid="1648628394364" I鈥�.

Draw a stepwise mechanism for the following reaction.

Elimination of HBr from 2-bromobutane affords a mixture of but-1-ene and but-2-ene. With sodium ethoxide as base, but-2-ene constitutes 81% of the alkene products, but with potassium tert-butoxide, but-2-ene constitutes only 67% of the alkene products. Offer an explanation for this difference.

Although there are nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane, one stereoisomer reacts 7000 times more slowly than any of the others in an E2 elimination. Draw the structure of this isomer and explain why this is so.

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.
See all solutions

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