What do these prefixes describe?

Vinyl

Allyl

Methylene

Vinyl= monosubstituted ethylenes (vinyl chloride= CH₂=CHCl)

Allyl= C3 substituted propylene (allyl bromide=

CH₂=CHCH₂Br)

Methylene= -CH₂ group (methylene cyclohexane= a cyclohexane with a CH₂ group...double bond from cyclic C to a CH₂)

Common names for ethene and ethyne.

When naming a molecule with both a double and triple bond in it, which gets the lower carbon number?

Ethene= ethylene

Ethyne= acetylene

When both in the same molecule, the double bond gets the lower number

CH₃CH=CH-C=C-CH₃

2-hexen-4-yne

What is a vicinal?

What is a geminal?

Why are geminals/hydrates not often seen?

Vicinals= diols with hydroxyl groups on adjacent carbons

Geminal aka hydrates= diols with hydroxyl groups on the same carbon

Geminals/hydrates not often seen because they spontaneously lose water and produce carbonyls.

What is an ether?

What is a 3-membered cyclic ether called?

Common names for:

methanal

ethanal

propanal

Ether=   R-O-R

3-membered cyclic ethers= oxiranes or epoxides - or ethylene oxide

Methanal= Formaldehyde

Ethanal= Acetaldehyde

Propanal= Propionaldehyde

Common names for:

2-propanone

methanoic acid

ethanoic acid

propanoic acid

2-propanone= acetone

methanoic acid= formic acid

ethanoic acid= acetic acid

propanoic acid= propionic acid

Prefix and suffix for:

esters

acyl halides

 amides

nitriles/cyanide

 thiols

imines

ethers

...and just prefixes for:

sulfides

nitros

azides

diazos

What are structural/confirmational isomers?

What are enantiomers?

Structure/confirmational isomers only share a molecular formula.

Enantiomers are chiral objects that are nonsuperimposable mirror images.

Put the following bases in order from strongest to weakest: RCO₂^-, ROH, HO^-, RO^-, H₂O

Put the following nucleophiles in order from strongest to weakest when in a protic solvent: CN^-, HO^-, Br^-, I^-, F^-, H₂O, Cl^-, RO^-

Put the following nucleophiles in order from strongest to weakest in when in an aprotic solvent: Cl^-, Br^-, F^-, I^-

Put the following leaving groups in order of best to worst:

Cl^-, Br^-, F^-, I^-

Base Strength:

RO^->OH^->RCO₂^->ROH>H₂O

Nucleophile strength in a protic solvent (larger atoms=stronger Nu in protic solvents:

CN^->I^->RO^->HO^->Br^->Cl^->F^->H₂O

Nucleophile strength in an aprotic solvent (strong bases=stronger  Nu in aprotic solvents):

 F^->Cl^->Br^->I^-

Leaving group strength (weak base=better LG):

I^->Br^->Cl^->F^-

Are SN1 and SN2 reactions favored in protic or aprotic solvents?

What happens to the stereochemistry of SN1 and SN2 reactions?

SN1 reactions are favored in polar protic solvents.

SN2 reactions are favored in polar aprotic solvents.

If the reactant is optically active, SN1 reactions produce racemic mixtures.

If the reactant is optically active, SN2 reactions produce a product with an inversion of stereochemistry (still optically active).

As you increase branching, what happens to the boiling point and density?

As molecular weight increases, what happens to the melting and boiling points and density?

More branching means decreased boiling point and decreased density (decrease the surface area so decrease intermolecular forces).

As molecular weight increases, melting and boiling points also increase and density increases.

Addition of cold, dilute KMnO₄ to an alkene yields...

Addition of hot, basic KMnO₄ to a non-terminal alkene...

Addn of cold, dilute KMnO₄ to an alkene yields a 1,2 diol (vicinal diol/glycol), syn orientation.

Addn of hot, basic KMnO₄ cleaves the non-terminal alkene to produce a carboxylic acid and carbon dioxide...if the double bonded carbon is disubstituted, it produces a ketone.

Steps for the addition of HX to an alkene.

Steps for the addition of X₂ to an alkene.

Addition of HX to an alkene:

step 1: Addn of H⁺ to less highly substituted C to form a stable C⁺ (Markovnikov's)

step 2: Addn of halide to the positive C

Addition of X₂ to an alkene:

step 1: double bond displaces X^- and forms a cyclic halonium ion

step 2: X^- attacks to form a dihalide compound in anti addition.

Steps for addition of H₂O to an alkene.

Steps for addition of a free radical (such as Br) to an alkene/alkyne.

Steps of hydroboration and what it produces.

Products of ozonolysis with Zn/H₂O.

Products of ozonolysis with NaBH₄/CH₃OH.

What do peroxycarboxylic acids (such as CH₃CO₃H and mcpba) do to alkenes? What is the product?

Polymerization occurs under...

How does the boiling point compare between internal alkenes/alkynes and terminal alkenes/alkynes?

Peroxycarboxylic acids oxidize alkenes and produce oxiranes.

Polymerization occurs under high temperatures and high pressures.

Internal alkenes/alkynes boil at higher temps than terminal alkenes/alkynes.

Constitutional isomers= different atom connectivity

Conformational isomers= different 3D arrangement

What are the structures of the following amine compounds:

Amide

 Carbamate/Urethane

Isocyanate

Enamine

Imine

Nitrile/Cyanide

Nitro

Diazo

Azide

Amide:  O       (carboxyl + amine)

            ||

          RCNR₂       

Carbamate/Urethane:   O      (Ester + amine)

                                    ||

                                ROCNR₂

Isocyanate:    R=O=C=NR  (add alcohol->carbamate)

Enamine:   R₂=CRNR₂ (amine equivalent of anenol)

Imine:  R₂C=NR  (carbon=nitrogen)

Nitrile/Cyanide:  C=N  (C triple bonded to N)

Nitro: -NO₂

Diazo: R₂C=N=N  (N₂ group)

Azide: R-N=N=N  (N₃ group)

alkyl halide + ammonia ->....+base->

(CH₃Br + NH₃ ->_____+NaOH->_____)

Alkyl halide + ammonia -> alkylammonium halide salt

alkylammonium halide salt + base -> alkyl amine

CH₃Br+NH₃-> CH₃NH₃⁺Br^-+NaOH-> CH₃NH₂ + NaBr +H₂O

What is Markovnikov's Rule?

What conditions often cause free radical addition?

Markovnikov's= When adding a protic acid HX to a double bond, the H will add to the less substituted carbon, and the X will add to the more substituted carbon after.

Peroxides, oxygen, and UV light cause free radical addition (which is anti-markovnikov...free radical adds before the free H).

How can you form an amine from a nitro compound?

How can you form an amine from a nitrile?

How can you form an amine from an imine?

Nitro compound + reducing agent such as Zn or Fe in dilute HCl turns the nitro group into a primary amine.

Nitrile compound + hydrogen and a catalyst or LAH creates a primary amine

CH₃CH₂C=N + LAH -> CH₃CH₂CH₂NH₂

Aldehyde or ketone + ammonia -> Imine

Imine + hydrogen and a catalyst -> amine

  O                      NH                              NH₂

  ||   +  NH₃ -> ||   + H₂-Ni/RaneyNi ->  |

RCR               RCR                             RCR

What is Zaitsev's Rule?

Describe the frequencies these bonds would absorb in an IR spectrum:

Carbonyl  (C=O)

Alcohol or Acid (O-H)

Amine (N-H)

Carbonyl (C=O) ~1750

 Alcohol or Acid (O-H) ~3000 (broad)

Amine (N-H) ~3000 (sharp)

Amide + LAH -> amine

  O

  ||     +  LAH ->

RCNH₂               RCNH₂