Organic Chemistry Exam 1

SP3 hybridized

• 4 hybrid orbitals

• 4 sigma bonds

• 0 Pi bonds

• ~109.5 bond angle

• tetrahedral

SP2 hybridized

• 3 hybrid orbitals

• 3 sigma bonds

• 1 Pi bonds

• 120 bond angle

• trigonal planar

SP

• 2 hybrid orbitals

• 2 sigma bonds

• 2 Pi bonds

• 180 bond angle

• linear

• Alkane

• Hydrocarbons that do not contain multiple bonds

• (-ane)

• Alkene

• Contain at least one C-C double bond

• (-ene)

• Alkyne

• Contain at least one C-C tiple bond

• (-yne)

• Aromatic

• Contain a special type of ring

• Ex: Benzene

• Haloalkane

• R-X(Halogen, e.g. F, Cl, Br, I…)

• Identify 1°, 2°, and 3° by identifying the number of carbons connected to the carbon connected to the halogen

• Alcohol

• R-OH

• (-ol)

• H-bonding properties

• Identify 1°, 2°, and 3° by identifying the number of carbons connected to the carbon connected to the OH group

• Polar

• Ether

• R-O-R’

• “Carbon on ether side of oxygen”

• H-bond ACCEPTOR, NOT DONOR

• Amine

• R-N

• (-amine)

• Identify 1°, 2°, and 3° by identifying the number of R groups connected to the carbon connected to the nitrogen

• Aldehydes

• O double bonded to a C with either an H on either side or 1 H and 1 C.

• (-al)
  

• Ketone

• O double bonded to a C with a C on either side.

• Carboxylic Acid

• O double bonded to a C with either a C/H on one side, and an OH on the other

• Amide

• O double bonded to a C with a C/H on one side and an N group on the other

• Identify 1°, 2°, and 3° by identifying the number of R groups connected to the N group

• Ester

• O double bonded to a C with a R/H on one side and an O-R group on the other

• Nitriles

• R-C(triple bond)N

• (-nitrile)

Functional Groups

• Alkene

• Alkyne

• Aromatic

• Alkane

• Haloalkane

• Alcohols

• Ethers

• Amines

• Aldehydes

• Ketones

• Carboxylic acids

• Amides

• Esters

• Nitriles

Degree of Unsaturation steps

1) Calculate full saturation CnH(2n+2)

2)

• If halogen in present +1H

• If O is present do nothing

• if N is present -1H

3) (Full saturation - actual formula)/2=u

Degree of unsaturation

Tells you how many Pi bonds you need or if you need a ring structure

Geometric Isomer

Same connectivity, but different spatial arrangement/orientation

Constitutional isomer

Same formula, but different connectivity

Formal charge equation

	=	formal charge
	=	number of valence electrons
	=	number of nonbonding valence electrons
	=	total number of electrons shared in bonds

IR O-H absorption

• 3600-3200 cm^-1

• Strong and BROAD

IR N-H

• 3500-3200 cm^-1

• medium

IR C-H Sp3

• 3000-2850 cm^-1

• Strong absorption

IR C-H Sp2

• 3150-3000 cm ^-1

• medium

IR C-H Sp

• 3300

• medium

IR C≡C

• 2250 cm^-1

• medium

IR C≡N

• 2250 cm^-1

• medium

IR C=O

• 1800-1650 (OFTEN ~1700)

• STRONG

IR C=C

• 1650 cm^-1

• medium

IR Aromatic/Benzene ring

• 1600,1500 cm^-1

• medium

1500-400 cm^-1 IR region

Fingerprint region on IR

IR methyls like isopropyl/geminal/tertbutyl

• 1375 cm^-1

• “Snake tongue”

IR Long C-H chains

• 720 cm^-1

• “rocking of the chain”

H+ absorption 12-9 ppm

Carboxylic acid (12-10) or Aldehyde(10-9)

H+ absorption 8-6.5 ppm

benzene ring(monosubstituted)/aromatic

H+ absorption 6-4.5 ppm

C=C

H+ absorption ~2.5 ppm

C≡C

H+ absorption 4-2.5 ppm

Methyl group with an N, O, or X on the end

H+ absorption 2.5-1.5 ppm

z=c-c-h z=C, O, N

H+ absorption ~1.7 ppm

Sp C-H bonds

H+ absorption ~1.3 ppm

Sp2 C-H bonds

H+ absorption ~0.9 ppm

Sp3 C-H

What base can fully deprotenate an alkyds/create one

2Na/NH2

2 HX (Hydrohalogenation)

Gives germinal dihalide alkane

2 X2 Halogenation

Tetrahalide. First trans as an intermediate with one equivalent.

H20/H2SO4(HgSO4) Hydration

Gives a ketone. Enol as an intermediate but through tautomerazation becomes ketone.

BH3/H2O2,OH- (Hydroboration Oxidation)

Gives ketone if internal, aldehyde if external. Also starts as enol but undergoes tautomerization.

Acetylide ions react in what kind of mechanism?

Sn2 (substitution unless the alkyl halide is 2° or 3°

2H2/Pd-C (reduction)

With an alkyne will give an alkane.

H2/Lindlar Catalyst

Reacts with alkyne to give a CIS alkene. Reacts with alkene to give SYN alkane.

Na/NH3

Reacts with alkyne to give trans alkene

LiAlH4/2H2O

Reacts with epoxies by opening the rings to make an alcohol