Orgo II Quiz 4 Cram

higher

amines have a ____ boiling point than ethers

lower

amines have a ____ boiling point than alcohols

less

if an amine is next to an electronegative group, it will be ____ basic

more, less

the ___ aromatic an amine is, the ____ basic it is

primary

this amine substitution is the least basic

secondary

this amine substitution is the most basic

EAS

what happens when you add Br2 to aniline

N attacks carbonyl C, Cl leaves

what happens when you add an acid chloride to aniline

it gets protonated

what happens when you put an amine in acid

base

PhLi is a ____

it gets deprotonated

what happens when you put an amine in a base

reductive amination

carbonyl is added to amine, selectively alkylates amine

N-methylaniline

aniline + formaldehyde --> ___

2 alcohols added to amine

what happens when two epoxides react with amine

N-isopropylpentanamine

acetone + pentanamine --> ___

carbinolamine

reductive amination transition state

C=N

Imines contain ____

CH3I overalkylates amine

first step of hofmann elimination

Add Ag2O, Ag bonds with I, leaves OH

second step of hofmann elimination

OH catalyzed E2 rxn, kicks off amine

third step of hofmann elimination

alkenes

hofmann eliminations turn amines into ___

acid chloride, amide

you can add a nitro group to aniline if you protect the amine by using an ____ to turn it into an ___

NaOH, H2O

amide + ____ --> amine

N2+

NH2 + NaNO2 --> ____

CuBr

R-N2+ + ____ --> R-Br

KMnOH

Ph-CH3 + ____ --> COOH

R-NO2

R-NH2 + 1)NaNO2, HCl 2)CuNO2 -->

H2, Ni

cyanide + ____ --> C-NH2

gabriel synthesis

uses deprotonated phthalimide as a nitrogen source and a good nucleophile to SN2 react only once with an electrophile of interest. Phthalic acid is removed via NAS in either acidic or basic conditions

aminoalcohol

Phthalimide + 1) KOH 2) epoxide 3) NaOH, H2O --> ___

acyl azide (N3C=O)

acid chloride + NaN3 --> ___

isocyanate

R-N=C=O is also known as ___

O=C=N-R

acyl azide + heat --> ___

R-NH2

O=C=N-R + H3O+, H2O --> ___

CH3CH2-NH2

CH3CH2-NO2 + H2, Li --> ___

alcohols, ethers, amines, alkyl groups, thiols, and halogens

Six examples of ortho/para directing groups

cyanide, carbonyls, NO2

three examples of meta-directing groups