Midterm Flashcards

Geometries in Trigonal Planar

trigonal Planar, bent

Geometries in Tetrahedral

Tetrahedral, trigonal pyramidal, bent

Geometries in Trigonal Bipyramidal

Trigonal Bipyramidal, Seesaw, T-shaped, Linear

Geometries in Octahedral

Octahedral, Square Pyramidal, Square Planar, T-shaped, Linear

Trigonal Planar

Bent

Tetrahedral

Trigonal Pyramidal

Bent

Trigonal Bipyramidal

Seesaw

T-shaped

Linear

Octahedral

Square Pyramidal

Square Planar

T-shaped

Linear

Hybridization of Linear

Sp

Hybridization of trigonal planar

Sp2

Hybridization of tetrahedral

Sp3

Hybridization of Trigonal bipyramidal

Sp3d

Hybridization of Octahedral

Sp3d2

Bond angle of tetrahedral

109\.5

Lone pair next to double bond

Lone pair next to positive charge

Positive charge next to pi bond

Pi bond btwn 2 atoms (1 is electronegative)

Alternating double/single bonds in a ring

Most important resonance form…

* more covalent bonds
* Complete valence shell
* No separation of charge
* Negative charge on electronegative atom
* Positive charge on less electronegative atom

Benzene ring (phenyl)

amine

Alcohol

ether

Alkyl halide

thiol

Ketone

Aldehyde

Ester

Carboxylic acid

Amide

Suffix of ether

ether

Suffix of aldehyde

\-al

suffix of ketone

\-one

Suffix of carboxylic acid

\-oic acid

Suffix of ester

\-oate

Suffix of amide

\-amide

Isopropyl Group

Sec-butyl group

tert-butyl group

Isobutyl group

Phenyl Group

Benzyl Group

Allyl Group

Nitrile

Neopentyl

Synthesis of Alkanes from Alkenes

Need H2 and metal catalyst

Synthesis of alkane from alkyne

2 equivalent H2 and metal catalyst

Total number of stereoisomers

2^n

Molecular formula for saturated hydrocarbon

CnH2n+2

chiral molecule exceptions

Allenes, Atropoisomer

Formula for max # of stereoisomers

2^n

Strong acids (5)

HI, HBR, HCL, H2SO4, tosic acid

Excellent leaving groups description

Weak bases, no charge when leave

Excellent nucleophiles description

Negative charge, less electronegativity, least bulky

SN1

Tertiary > secondary > primary, polar protic solvents, weak nucleophile

SN2

Methyl > primary > secondary, polar aprotic solvent, strong nucleophile

Strong Nucleophile, poor base

Cl-, Br-, I-, H2S, HS-, RSH, RS-, CN-, N3-, carboxylates

Good base, poor nucleophile

NaH, tBuO-, Lithium diisoropylamide (LDA)

Strong nucleophile, strong base

OH-, RO-

Primary LG with strong nucleophile and strong base

SN2

secondary LG with strong nucleophile and strong base

E2 and SN2

tertiary LG with strong nucleophile and strong base

E2

weak nucleophile and weak base

H2O, ROH, carboxylic acids

primary LG with weak nucleophile and weak base

SN2

secondary LG with weak nucleophile and weak base

SN1 + E1

tertiary LG with weak nucleophile and weak base

SN1 + E1

HX reagent with alkene

Alkene → alkyl halide

Markovnikov

Alkene + H2O + acid

Alkene → Alcohol

Markovnikov

Rearrangements

X2 (dihalide) + alkene

Alkene → dihaloalkane

Vicinal dihalide

Anti-addition

X2+ H2O + Alkene

Alkene → halohydrin

Markovnikov

X2+ ROH + Alkene

Alkene → ether

1) Hg(OAc)2 THF-H2O, 2) NaBH4, OH-

Oxymercuration-demurcuration

Alkene → alcohol

Anti-addition

Markovnikov

1) Hg(OAc)2 THF-ROH, 2) NaBH4, OH-

Solvomercuration-demurcuration

Alkene → ether

1) BH3-THF 2) H2O2, OH-

Hydroboration-oxidation

Alkene → alcohol

Syn addition

Anti-Markovnikov

1)OsO4, pyridine 2) NaHSO3, H2O

1,2,-dihydroxylation of alkene

Alkene → 1,2,diol

OsO4 + NMO

Alkene → 1,2 diol

KMnO4 + base, cold

Alkene → 1,2-diol

1) KMnO4, OH-, H2O, heat 2) H2O+

Oxidative cleavage of alkene

Hard oxidation

Alkene → carboxylic acid, ketones, co2

H → oh

1) O3, CH2CL2, cold 2) Me2S

Ozonolysis

Alkene → ketone, aldehydes

H stays H

alkyne + excess X2

Tetrahaloalkane

Anti addition

Alkyne + HX

Vinyl halide

Markovnikov

Alkyne + excess HX

Gem-dibromide

Markovnikov

Alkyne + HX + peroxides

Vinyl Halide

Anti-markovnikov

1) NaNh2 in NH3 2) R’-X

Carbon extension

Lindlar’s catalyst, H2

Alkyne → cis alkene

Na/NH3 OR Li, EtNH2 cold OR NH4CL

Trans alkene

PBr2 and SOCl2

Replace OH with Br/Cl

MsCl, TsCl

Convert alcohols to good leaving groups

OR- + X-R

Williamson ether synthesis