C1: Structure and Bonding

Question 1

how do you name an alkane?

Answer 1

CHECK FOLDER

Question 2

how do you name a cycloalkane?

Answer 2

same rules as alkanes but add suffix “cyclo”

Question 3

how do you name an alcohol?

Answer 3

• number the chain so OH groups get the lowest #
• change “ane” suffix to “ol”

Question 4

how do you name an ether?

Answer 4

CHECK FOLDER

Question 5

how do you name an aldehyde?

Answer 5

• the C with the double bonded O is #1 and does not need to be numbered
• add the suffix “al”

Question 6

how do you name a ketone?

Answer 6

• number the chain so the C with the double bonded O is the lowest #
• add the suffix “one”

Question 7

how do you name a carboxylic acid?

Answer 7

• the C with the double bonded O is #1 and does not need to be numbered
• add the suffix “oic acid”

Question 8

how do you name an ester?

Answer 8

CHECK FOLDER

Question 9

what is bond dissociation energy?
bonds have a higher BDE when:
- orbitals have a greater/smaller overlap
- they have higher/lower s character
- more/less electrons are shared
- they are shorter/longer in length

Answer 9

• the energy required to break a bond
• greater
• higher
• more
• shorter

Question 10

what do Z and E mean within an organic molecule?

Answer 10

on a C-C double bond,
after determining the priority group(s),
Z= substituents on zame zide
E= substituents on opposite sides

Question 11

list the compounds from strongest acid/ good proton donor to weakest acid/poor proton donor
- this order is also the order of….

Answer 11

• CHECK FOLDER
• weakest conj base/ most stable to strongest conj base/ least stable

Question 12

what is a conjugated molecule?
- what are the 2 requirements to be met in order for a molecule to be conjugated?
- how is a conjugated molecule stabilized?
- if an atom has ____ and is next to sp2 atoms it itself can also be sp2

Answer 12

a molecule that has 3 or more overlapping and parallel p orbitals (3 connected sp2 atoms)
- molecule has to be planar
- molecule needs 3 or more adjacent sp2 atoms
- by having more resonance structures, the more they have the more stable they are
- lone pairs or a charge

Question 13

what are the 4 rules that need to be satisfied for the most stable resonance structure?

Answer 13

1. satisfies octet rule for all atoms
2. has less separation of charge (less charges= more stable)
3. has a negative charge on a more electronegative atom
4. has a positive charge on a less electronegative atom

Question 14

____ can be stabilized by resonance, making the original acid more likely to ____ and thus a ____

Answer 14

conjugate bases; give up a proton; stronger acid

Question 15

what is induction?

Answer 15

electron withdrawal or donation through bonds, can be stabilizing or destabilizing

Question 16

for induction,
what are 3 examples of electron donating groups?
- what do these examples of EDG stabilize?
- what do these examples of EDG destabilize?
- what are the answers to these questions for electron withdrawing groups?

Answer 16

• less electronegative atoms, r groups, atoms with lone electron pairs
• electron deficient atoms: carbocations, radicals, pi bonds
• electron rich atoms: carbanions
• the opposite of everything

Question 17

within induction,
if the molecule has an r group that is electron donating and has carbocations, radicals, or pi bonds.. is it stabilized or destabilized?

Answer 17

stabilized

Question 18

within induction,
if the molecule has an r group that is electron donating and has carbanions.. is it stabilized or destabilized?

Answer 18

destabilized

Question 19

what does electron withdrawal mean?

Answer 19

that the r groups are getting closer

Question 20

what does an equatorial bond look like?
- axial?

Answer 20

• horizontal, out to the side
• vertical, alternating up/down

Question 21

for stability within a molecule, should the smaller/larger group be axial/equatorial in order to be more stable?

Answer 21

the smaller group should be axial

Question 22

when there are at least 2 chair conformations for a molecule that partake in a ring flip,
what happens to the axial/ equatorial positions?

Answer 22

they switch, equatorial become axial and vice versa

Question 23

what is steric strain?
- does is stabilize/ destabilize?
- the largest groups will be ____ to each other and ____ if possible

Answer 23

electron- electron repulsion that occurs when groups get close to each other
- destabilize
- anti; equatorial

Question 24

describe what anti looks like within a molecule
- gauche?

Answer 24

• anti is directly across from each other
• gauche is right next to each other

Question 25

newman projections look….

Answer 25

down C-C bonds

Question 26

what is the orientation in space of hashes and wedges on a molecule?

Answer 26

hashes go into the page (back) and wedges come out of the page (forward)

Question 27

what is ring strain?
- what is the trend in stability?
- the more points a molecules ring has, the more ____ is stored within each molecule

Answer 27

• strain produced by deviations from 109.5 degrees in cycloalkane rings that cause instability
• the higher the # of points on a ring (ex 6 membered ring), the more stable and least ring strain
• energy

Question 28

how do you name a carboxylic acid?

Answer 28

• the C with the double bonded O is #1 and does not need to be numbered
• add the suffix “oic acid”

Question 29

a small pKa means a molecule is more ____

Answer 29

acidic

Question 30

a chair conformation is always more stable than a ____

Answer 30

boat conformation

Question 31

• CHO is a shortcut for naming a/an ____
• COOH is a shortcut for naming a/an ____
• COOR is a shortcut for naming a/an ____

Answer 31

• aldehyde
• carboxylic acid
• ester