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organic > Chapter 9 > Flashcards

Chapter 9 Flashcards

1
Q

nucleophile

A

donates electron pair

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2
Q

substrate

A

reacts with reagent

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3
Q

hindered

A

creates difficulty for a free floating molecule to attack…

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4
Q

unhindered

A

free floating molecule can attack molecule easier

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5
Q

poor nucleophile

A

H2O, RC=OOH, ROH

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6
Q

weak base good nucleophile

A

-CN,N3-, RSH, R3P, RNH2, RS-, RC(triplebond)C-,

Cl-<I-

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7
Q

strong basic unhindered nucleophile

A

-OH,-ORprimary, RNH

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8
Q

strong basic hindered nucleophile

A

look on page

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9
Q

good leaving groups

A

I,Br,Cl, OH2, HOR, HOC=OR, OO=S=OR, R=CH3, HEXANECH3,

RARE: OH and OR

(not all listed look on page)

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10
Q

Methyl

poor nucleophile, weak base good nucleophile, strong base unhindered nucleophile, strongly basic hindered nucleophile

A

poor nucleophile: No RXN
weak base good nucleophile: SN2
strongly basic unhindered nucleophile: SN2
strongly basic hindered nucleophile: SN2

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11
Q

Primary Unhindered

poor nucleophile, weak base good nucleophile, strong base unhindered nucleophile, strongly basic hindered nucleophile

A

poor nucleophile: No RXN
weak base good nucleophile: SN2
strongly basic unhindered nucleophile: SN2
strongly basic hindered nucleophile: E2

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12
Q

Primary Hindered

poor nucleophile, weak base good nucleophile, strong base unhindered nucleophile, strongly basic hindered nucleophile

A

poor nucleophile: No RXN
weak base good nucleophile: SN2
strongly basic unhindered nucleophile: E2
strongly basic hindered nucleophile: E2

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13
Q

Secondary

poor nucleophile, weak base good nucleophile, strong base unhindered nucleophile, strongly basic hindered nucleophile

A

poor nucleophile: slow for Sn1/E1
weak base good nucleophile: SN2
strongly basic unhindered nucleophile: E2
strongly basic hindered nucleophile: E2

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14
Q

Tertiary

poor nucleophile, weak base good nucleophile, strong base unhindered nucleophile, strongly basic hindered nucleophile

A 
poor nucleophile: Sn1/E1
weak base good nucleophile: Sn1/E1
strongly basic unhindered nucleophile: E2
strongly basic hindered nucleophile: E2
SBHN Hoffman
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organic (5 decks)

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