CHM 2211L / CHM 2211L MIDTERM REVIEW

CHM 2211L MIDTERM REVIEW


Protic solvents

- can participate in H-bonding
- H bonded to O,N,F


Aprotic solvents

- cannot hydrogen bond
- no O-H or N-H bonds


Hydrogen bond donor

- hydrogen directly bonded to a N, O, or F atom


Hydrogen bond acceptor

- a lone pair of electrons associated with an electronegative atom

HNMR - if chiral center (bond attached to four different things) is present,

- the 2 H's on a CH2 group are not equivalent


HNMR <----

- higher frequency
- higher shift
- deshielded
- downfield


HNMR --->

- lower frequency

,- lower shift
- shielded
- upfield


An electronegative atom (Cl) will ____ protons

- deshield


Protons now have greater delta energy between spin states (shift left) ==

- larger frequency absorbed


Integration

- area under each signal
- tells us the number of protons in that signal


Calculation of degrees of unsaturation

- {(#carbons)(2) + 2) - #H} / 2


Degrees of unsaturation; for each halogen, add

-1


Degrees of unsat.; for each nitrogen, subtract

- one hydrogen


Lucas test: positive test

- secondary or tertiary alcohol; 2nd layer will form


lucas test: negative test

, - primary alcohols

Jones oxidation: + test

- 1st/2nd alcohols
- solution turns from orange -> green/blue


Jones oxidation:

- test - 3 alcohols


Ferric chloride: + test

- phenol present; solution turns to red/green/blue/purple


Tollens test: +

- aldehyde ; silver precipitate forms


2,4 - DNP: +

- aldehyde or ketone; orange ppt


Semicarbazone +

- aldehyde or ketone; ppt forms


Iodoform +

- methyl carbonyl; yellow ppt


Caffeine HBA, HBD

- 5,0

Salicyclic acid HBA HBD