Fill in the missing information & name the mechanism type:
NaSCH3
CH3-CH2-Cl ----------> ?
DMSO
What is CH3-CH2-SCH3 and Sn2 ?
100
________ tells us which functional groups are present in a molecule, while _______ essentially shows a map of the carbon-hydrogen framework of a molecule.
What is IR and NMR?
100
_____ is a polar solvent without an H on N, O, or X whereas _____ is a polar solvent with an H on N, O, or X.
What is polar aprotic solvent & polar protic solvent
100
Put the following radical species in order from least stable to most stable: CH3, secondary, primary, allylic, tertiary, benzylic.
What is
CH3 < Primary < Secondary < Tertiary < Allylic < benzylic?
200
R R R R
| | ? | |
C=C -----> C=O + O=C
| | | |
R R R R
What is 1. O3 2. Zn/H3O+ ? (Oxidative Cleavage)
200
Fill in the missing information & name the mechanism type:
CH3 CH3 CH3
| ? | |
CH3-C--Cl ----> CH3-C-OH + CH3-C--OH *(--) bonds go
| | | into the board
H H H & (-) bonds
go outward
What is H2O and Sn1?
200
Determine the unknown compound from the following data:
C4H8O2
IR: 1743 cm-1
NMR: 3H, singlet, 3.7ppm
2H, quartet, 2.35ppm
3H, triplet, 1.15ppm
What is CH3-C-O-CH2CH3
ll
O
200
A carbon one away from the leaving group/carbocation carbon.
What is beta-carbon
200
________ or _______ could be used to convert a secondary alcohol into a ketone.
What is [Ox] or PCC?
300
OH H
? | |
CH2=CH2 -----> H--C----C--H
| |
H H
What is 1. Hg(OAc)2, H2O/THF 2. NaBH4 or H3O+/H2O or H2O/H2SO4 ? (Oxymercuration)
300
Fill in the missing information & name the mechanism type:
CH3 Br H2O
| | CH3OOH
CH3-CH----C-CH3 -----------> ?
| Heat
H
What is
CH3
|
CH3-C=C-CH3 & E1?
|
H
300
Determine the unknown compound from the following data:
C4H11N
IR: 3310 cm -1 (weak), 3340 cm-1 (weak)
NMR: 3H, triplet, 0.9ppm
3H, doublet, 1.12ppm
2H, quintet, 1.62ppm
2H, broad singlet, 2.0ppm
1H, sextet, 2.8ppm
What is CH3
l
CH2
l
CH3-CH-NH2
300
Give the IUPAC name of the following molecule.
CH2CH3
l
CH3-CH-CH-CH2CH2-CHCH3
l l
I I-CHCH2CH3
What is 3-ethyl-2,7-diido-6-methylnonane
300
A molecule with two OH substituent is _______, a molecule with an OH and an OR substituent is _______, and a molecule with two OR substituent is _______
What is hydrate, hemiacetal, & acetal.
400
a? b?
CH3--CH=CH2 --> CH3--CH2--CH2--OH --> CH3--CH2--C=O
|
H
What is a.) 1. BH3, THF 2. H2O2, NaOH, H2O and b.) PCC ?
400
Fill in the missing information & name the mechanism type:
TosO CH3
| ? |
CH3-CH2-C-CH3 --------> CH3-CH2-C=CH2
|
CH3
What is t-BuO-/heat and E2?
400
Determine the unknown compound from the following data:
C5H7NO2
IR: 1747 cm-1, 2250 cm-1 (short, thin)
NMR: 2H, quartet, 4.28ppm
2H, singlet, 3.4ppm
3H, triplet, 1.32ppm
What is CH3CH2-O-C-CH2-CN
ll
O
400
Give the IUPAC name of the following molecule.
O
ll
CH3CH2CH2CH2CH2CH2CH2CH2CH-CH
l
CH3
What is a.) Br2, light b.) t-buO-, heat c.) 1. BH3, THF 2. H2O2, NaOH, H2O ?
500
Sn1 and E1 are not possible with primary L.G.'s because primary carbons form _______. Sn2 is not possible with tertiary L.G.'s because tertiary carbons are too _________. Solvents that are _________ favor Sn1 and E1, while _______ solvents favor Sn2 and E2. Lastly, ______ will always favor elimination over substitution.
What is......
Sn1 and E1 are not possible with primary L.G.'s because primary carbons form UNSTABLE CARBOCATIONS. Sn2 is not possible with tertiary L.G.'s because tertiary carbons are too STERIC HINDERED. Solvents that are POLAR PROTIC favor Sn1 and E1, while APROTIC solvents favor Sn2 and E2. Lastly, HEAT will always favor elimination over substitution.
500
Determine the unknown compound from the following data:
C6H12O
NMR Spectrum: IR Spectrum:
doublet, 1.07 ppm (6H) Strong peak near
triplet, 1.11 ppm (3H) 1720 cm-1.
quartet, 2.44 ppm (2H)
Septet, 2.58 ppm (1H)
What is
CH3
|
CH-----C=O
| |
CH3 CH2CH3
500
Give the structure of 3-methyl-2-hexanone
What is CH3
l
CH3CH2CH2CH-C-CH3
ll
O
500
The correlation between basicity and leaving group reactivity is that the ______ the base, the _____ reactive the leaving group.