Block 1 - Foundations

Question 1

Anhydride functional group

Answer 1

O O
ll ll
C-C-O-C-C

Question 2

anhydride nomenclature

Answer 2

alkanoic anhydride

Question 3

nitrile functional group

Answer 3

-C=_N

Question 4

nitrile nomenclature

Answer 4

alkane nitrile

Question 5

thiol functional group

Answer 5

-C-SH

Question 6

thiol nomenclature

Answer 6

alkane-n-thiol

Question 7

phenol functional group

Answer 7

benzene ring with -OH

Question 8

phenol nomenclature

Answer 8

alkylphenol

Question 9

nomenclature priority

Answer 9

-COOH > ester > amide > nitrile > -CHO > ketone > alcohol > amine > C=C > alkyne > alkane > ether > alkyl halide = alkyl

Question 10

DBE formula

Answer 10

1/2 (2n4 + n3 - n1 + 2)

Question 11

newman projection terminology

Answer 11

staggered vs. eclipsed (anti, gauche and syn)

Question 12

electrostatic potential map colours

Answer 12

red = electron-rich (high electron density)
blue = electron-poor (low electron density)

Question 13

types of intermolecular forces

Answer 13

• momentary dipole-dipole attractions (dispersion forces)
• dipole-dipole interactions
• hydrogen bonding

Question 14

chromatography components

Answer 14

• solvent/mobile liquid phase = relatively non-polar

- absorbent/solid stationary phase = polar

Question 15

chromatography mechanism

Answer 15

if solute is:

• polar = more strongly attracted to polar stationary phase thus moves slowly
• non-polar = less attracted to polar stationary phase thus moves rapidly

Question 16

substitution bond changes

Answer 16

same type of bonds (sigma) broken and formed

Question 17

substitution DBE changes

Answer 17

DBE remains same

Question 18

addition bond changes

Answer 18

1 pi bond broken and 2 sigma bonds formed

Question 19

addition DBE changes

Answer 19

DBE decreases

- product less unsaturated/more saturated

Question 20

elimination bond changes

Answer 20

2 sigma bonds broken and 1 pi bond formed

Question 21

elimination DBE changes

Answer 21

DBE increases

- product more unsaturated

Question 22

reaction subclassifications

Answer 22

1) polar/non-polar
2) nucleophilic/electrophilic reagent
3) nature of substrate (alkyl - chain base, aryl - aromatic ring etc.)

Question 23

conditions of aromatic ring

Answer 23

• planar
• cyclic
• all atoms have p orbital
• ring contains pi electrons

Question 24

non-polar reactions

Answer 24

• reactions of free radicals

- bond breaking/making may take place simultaneously

Question 25

free radicals

Answer 25

neutral species with an unpaired electron

Question 26

polar reactions

Answer 26

- one bonding partner supplies electron pair while the other receives it to form a new bond - reaction between nucleophile and electrophile to form a new covalent bond

Question 27

nucleophile

Answer 27

- nucleus (+ve charge) lover | - electron rich: either neutral or -vely charged and have either lone e- pair or e- in pi bonds

Question 28

electrophile

Answer 28

- electron lover | - neutral or +vely charged

Question 29

types of bond cleavage

Answer 29

- symmetrically: homolytic bond cleavage | - unsymmetrically: heterolytic bond cleavage

Question 30

homolytic bond cleavage

Answer 30

- 1 e- ends up on each formerly bonded atom | - non-polar reactions

Question 31

heterolytic bond cleavage

Answer 31

- both e-s end up on one of the formerly bonded atoms - polar reactions - e- s move towards more electronegative atom - carbocations more common than carbanion as C is not very electronegative

Question 32

determination of nucleophilic/electrophilic reactions

Answer 32

determined by reagent/species doing the replacing | - if unsure, check other reactant as they will be opposites

Question 33

reaction mechanisms

Answer 33

detailed pathway by which reactants are converted to products - often require multiple steps (elementary reactions) that require multiple steps - reactive intermediates are unstable and short-lived (formed in one step then used up in the next)

Question 34

types of nucleophilic substitution

Answer 34

Sn1 and Sn2

Question 35

Sn1

Answer 35

stepwise so bond breaking THEN bond making

Question 36

Sn2

Answer 36

single step so bond breaking/forming simultaneous

Question 37

alkenes and alkynes are

Answer 37

nucleophiles (electron rich - e-s in pi bond) thus undergo electrophilic addition

Question 38

bonds in benzene

Answer 38

in reality, 6 identical 1.5 bonds but drawn as 1 of 2 resonance forms

Question 39

resonance energy

Answer 39

conjugated double bonds give extra stability

Question 40

simple benzene nomenclature

Answer 40

___benzene (e.g bromobenzene)

Question 41

complex benzene nomenclature

Answer 41

phenyl____

Question 42

benzene common names

Answer 42

- NH2 = aniline - CHO = benzaldehyde - CO2H = benzoic acid - OH = phenol - CH3 = toluene

Question 43

disubstituted benzenes

Answer 43

- 1,2-substituted = ortho - 1,3-substituted = meta - 1,4-substituted = para

Question 44

why are double bonds more polar?

Answer 44

relative mobility of pi electrons as they are not held as tight being further from the nuclei