ALL Organic Chemistry Flashcards (DAT)

Compounds with the same molecular formula but different connectivity of atoms

constitutional isomer

A single bond includes (# sigma/pi) bond(s)

one sigma

A double bond includes (# sigma/pi) bond(s)

one sigma and one pi

A triple bond includes (# sigma/pi) bond(s)

one sigma and two pi

Molecular geometry of NH3

trigonal pyramidal

Molecular geometry of C=C

trigonal planar

In nonpolar solvents, a ___ (shorter/longer) hydrocarbon is more soluble

longer

Acid base reactions favor the formation of ___ acids

weak

Weak acids have a ___ pKa

high

List the common functional groups in order of increasing acidity

amides, ester, ketone, aldehyde, carboxylic acid

EDG ___ (increase/decrease) the acidity of a molecule

decrease

EWG ___ (increase/decrease) the acidity of a molecule

increase

Acronym to remember acidity trends

CARDIO

___ (more/less) positive charge = strong acid

more

___ (large/small) atomic radius = strong acid

large

___ (high/low) electronegativity = strong acid

high

___ (more/less) resonance = strong acid

more

The ___ (more/less) electronegative atoms in a molecule, the more acidic

more

List the orbital hybridization in order of increasing acidity

sp3, sp2, sp

Equilibrium favors the ___ (keto/enol) form

keto

In IUPAC nomenclature, which has higher priority: amide or aldehyde

amide

In IUPAC nomenclature, which has higher priority: ester or ketone

ester

In IUPAC nomenclature, which has higher priority: ketone or aldehyde

aldehyde

In IUPAC nomenclature, which has higher priority: alcohol or ketone

ketone

In IUPAC nomenclature, which has higher priority: alkyne or alkene

alkene

Name the following compound

spiro[3.4]octane

Name the following compound

bicyclo[3.3.0]octane

Name the following compound

cyclohexanecarboxylic acid

Name the following compound

cyclohexanecarboxamide

List the prefix and suffix for aldehydes

oxo, al

List the prefix and suffix for ketones

oxo, one

List the prefix and suffix for alcohols

hydroxy, ol

List the prefix and suffix for amines

amino, amine

List the prefix for ethers

alkoxy

List the prefix for NO2

nitro

List the suffix for carboxylic acids

oic acid

List the ending word for acid anhydrides

anhydride

List the suffix for esters

oate

List the suffix for acid halides

oyl hallide

List the suffix for amides

amide

List the suffix for nitriles

nitrile

List the prefix and suffix for SH

mercapto, thiol

List the suffix for SO3H

sulfonic acid

List the suffix for sulfides

alkylthio

The common name for this compound

acetic acid

The common name for this compound

formic acid

The common name for this compound

acetone

The common name for this compound

formaldehyde

The common name for this compound

acetaldehyde

The common name for this compound

anisole

The common name for this compound

toluene

The common name for this compound

styrene

The ideal C-C-C bond is ___º

109.5

When a chair is flipped, all substituents pointing up ___ (stay up/become down)

stay up

When a chair is flipped, all axial substituents ___ (stay axial/become equatorial)

become equatorial

These compounds have an internal plane of symmetry

meso

Non-superimposable mirror images that have opposite configuration at all chiral centers

enantiomers

Stereoisomers that are not mirror images; have opposite configuration at some chiral centers

diastereomers

The maximum number of stereoisomers =

2^# chiral centers

Nucleophiles are electron-___

rich

Electrophiles are electron-___

poor

Nucleophiles ___ (accept/donate) electrons

donate

Electrophiles ___ (accept/donate) electrons

accept

Nucleophile strength ___ (increases/decreases) left to right across a row for both polar protic and polar aprotic solvents

decreases

I-, Cl-, Br-, HO-, HS-, and NC- are all examples of common

nucleophiles

H3C-CO-CH3, secondary LG, and tertiary carbocations are all examples of

electrophiles

___ ___ solvents form Hydrogen bonds

polar protic

___ ___ solvents cannot donate Hydrogen bonds

polar aprotic

For polar protic solvents, nucleophilicity increases ___ (up/down) a group

down

For polar aprotic solvents, nucleophilicity increases ___ (up/down) a group

up

Atoms that detach from the molecule, taking electrons

leaving groups

List three examples that are both nucleophiles and leaving groups

I-, Cl-, Br-

The best leaving groups are ___ ___

weak bases

The major, more substituted alkene product formed during an elimination reaction is called a ___ alkene

Zaitsev

You can produced the major, more substituted Zaitsev alkene through elimination with the following reagent(s)

H2SO4, heat

Draw the mechanism and name the product for the following reaction

but-2-ene

Is the following mechanism showing a dehydration or hydration reaction of an alcohol

dehydration

SN2 reactions are well known for their ___ ___

backside attack

SN2 reactions are ___ step(s)

one

In an SN2 reaction, stereochemistry ___ (is/is not) inverted

is

SN2 rate equation: rate =

k[nucleophile][substrate]

SN2 reactions are favored by ___ (strong/weak) nucleophiles

strong

SN2 reactions are favored by ___ (1/2/3) carbon substrate types

1

Common solvents for SN2 reactions include polar ___ solvents such as ___ and ___

aprotic

In SN___ and E___ reactions, the LG leaves once the nucleophile has attacked

2

SN1 reactions are ___ step(s)

two

SN1 reactions form a ___ mixture

racemic

SN1 reaction rate equation: rate =

k[substrate]

SN1 reactions are favored by ___ (strong/weak) nucleophiles

weak

SN1 reactions are favored by ___ (1/2/3) carbon substrate types

3

In SN___ and E___ reactions, the LG leaves on it’s own

1

In SN2, the rate determining step is the formation of the

carbocation

More stable carbocations allow SN1 reactions to happen ___ (faster/slower)

faster

Carbocation rearrangements only happen in what two reaction types

SN1 and E1

A hydride shift is the movement of a

hydrogen

E2 reactions are ___ step(s)

1

E2 reaction rate equation: rate =

k[base][substrate]

E2 reactions are favored by strong ___ ___

bulky bases

NaOEt and NaOMe are common bases for ___ reactions

E2

E2 reactions are favored by ___ (1/2/3) carbon substrate types

any