Chapter 4

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Total cards: 24•Content version: v4•Public deck•Updated: 8/1/2026

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Front (Question)

curved arrows

Back (Answer)

a bond is forming or breaking

Front (Question)

4 main ways electrons move in polar reactions

Back (Answer)

• nucleophilic attack • loss of leaving group • proton transfer (acid/base) • rearrangements

Front (Question)

nucleophilic attack

Back (Answer)

nucleophile attacks an electrophile (tail of arrow starts on electrons and end on the nucleus to share a bond)

Front (Question)

loss of a leaving group

Back (Answer)

heterolytic bond cleavage, an atom or group takes an electron pair (creates more lone pairs)

Front (Question)

proton transfers

Back (Answer)

the deprotonation of a compound (proton removed and electrons added?)

Front (Question)

rearrangements

Back (Answer)

carbocations can be stabilized by neighboring groups through slight orbital overlapping called hyperconjugation

Front (Question)

homolytic cleavage

Back (Answer)

half arrows, movement of free radicals

Front (Question)

heterolytic cleavage

Back (Answer)

full arrows, result in ions

Front (Question)

stability of free radicals

Back (Answer)

3>2>1>methyl

#10

Front (Question)

stability of carbocations

Back (Answer)

3>2>1>methyl+

#11

Front (Question)

stability of carbanions

Back (Answer)

-methyl>1>2>3

#12

Front (Question)

Steps to Chlorination of Methane

Back (Answer)

• initiation • propogation • termination

#13

Front (Question)

Chlorination of Methane: initiation

Back (Answer)

generates a radical

#14

Front (Question)

Chlorination of Methane: propogation

Back (Answer)

• something we made + something we started with to produce something reactive • will go until terminated

#15

Front (Question)

Chlorination of Methane: termination

Back (Answer)

side reactions that destroy the reactive intermediate

#16

Front (Question)

Energy for the Chlorination of Methane: lower the Ea, _______ the rate, so more __________ intermediate is formed

Back (Answer)

faster, stable

#17

Front (Question)

Hammond Postulate: endothermic

Back (Answer)

transition state resembles the product

#18

Front (Question)

Hammond Postulate: exothermic

Back (Answer)

transition state resembles the reactant

#19

Front (Question)

radical inhibitor

Back (Answer)

an inhibitor combines with a free radical to form a more stable molecule, create a slow endothermic reaction

#20

Front (Question)

early transition states are often a characteristic of fast _________ processes, while late transition states are often a characteristic of reverse

Back (Answer)

exothermic

#21

Front (Question)

the hammond postulate states that reactions which are thermodynamically _________________ and kinetically slow have transition states that occur late in the reaction time frame and resemble the products

Back (Answer)

endothermic

#22

Front (Question)

carbocation

Back (Answer)

positively charged carbon

#23

Front (Question)

carbocation: inductive effect

Back (Answer)

stabilizesa carbocation by the donation of electron density along sigma bonds

#24

Front (Question)

carbocation: hyperconjugation

Back (Answer)

stabilizes a carbocation by an overlap of sigma bonding orbitals with empty p orbitals