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Organic Chem > Test 2 > Flashcards

Test 2 Flashcards

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1
Q

which bonds are rigid

A

double and triple bonds

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2
Q

which bonds are flexible

A

single bonds

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3
Q

greater orbital size mismatch = _________ bond length

A

longer

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4
Q

greater orbital size mismatch = ________ bond strength

A

weaker

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5
Q

as pH decreases, acid strength ______

A

increases

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6
Q

as pKa decreases, acid strength ______

A

increases

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7
Q

factor of acidity =

A

10^ delta pKa (absolute value)

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8
Q

hydrocarbon definition

A

molecule with ONLY hydrogen and carbon atoms

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9
Q

what atom is going to “attack”

A

the LESS electronegative atom
LESS electronegative atom = less greedy, more willing to share

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10
Q

single bond C atom hybridization

A

sp3

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11
Q

double bond C atom hybridization

A

sp2

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12
Q

triple bond C atom hybridization

A

sp

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13
Q

weaker acid has a _____ conjugate base

A

stronger

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14
Q

stronger acid has a _____ conjugate base

A

weaker

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15
Q

requirement to be a bronstead base

A

at least one lone pair

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16
Q

requirement to be a bronstead acid

A

at least one hydrogen tom

17
Q

electrophile (lewis acids)

A

A+
A incomplete octet

17
Q

nucleophile (lewis base)

A

A- long pair
A lone pair
A=A
A=-A

18
Q

term for molecule that can act as an acid or a base

A

amphoteric

19
Q

resonance stabilization = ______ pKa

A

lower
aka more stable

20
Q

examples of resonance stabilization

A

negative charge stabilized by:
- placement on electronegative atom
- electronegative atom nearby
- double or triple bond nearby

21
Q

which orbital is the lowest energy
(best/most stabilizing)

A

sp

22
Q

most unstable cycloalkane

A

cyclopropane

23
Q

most stable cycloalkane

A

cyclohexane
cyclopentane is close second

24
Q

why are 10+ carbon rings unstable

A

trans angular sterics (clash)

25
Q

reasons cyclopropane is unstable

A

angle strain
torsional strain

26
Q

reasons cyclobutane is unstable

A

angle strain
torsional strain

27
Q

describe angle strain and torsional strain for cycloPROPANE

A

angle strain - too narrow, should be 109 degrees but they are 60 degrees

torsional strain - due to eclipsed (bent) bonds

28
Q

describe angle and torsional strain for cycloBUTANE

A

angle strain - too narrow, should be 109 degrees but they are 88 degrees

torsional strain - due to eclipsed (bent) bonds, molecule becomes puckered to remove some torsional strain (butterfly conformation)

29
Q

how does a double or triple bond affect planarity

A

atoms bonded to double or triple bonds are IN PLANE with the double or triple bond

30
Q

conjugate acids have ______

A

more H atoms

31
Q

conjugate bases have ______

A

fewer H atoms

Organic Chem (6 decks)

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