Exam 1 Review

HCl

-7

H3O+

0

-COOH

5

NH4+

9

phenol

10

R-SH

11

R-NH3+

11

H2O

14

R-OH

17

R-C - - - C-H

26

NH3

36

CH4

60

less than 0

protonated alcohol, carboxylic acid, water

~5

carboxylic acid

~10

protonated amine

~15

alcohol, water

~40

amine

Alkene

Alkyne

Amine

Ether

Aldehyde

Ketone

Carboxylic acid

Ester

Amide

sp3 no lone pairs

109.5, tetrahedral

sp3 1 lone pair

107, trigonal pyramidal

sp3 2 lone pairs

104.5, bent

sp2 no lone pairs

120, trigonal planar

sp2 1 lone pair

<120, bent

sp

180, linear

B/Al/C+

make 3 bonds, have empty p orbital

Does molecule H-bond with water?

O/N atom w/ lone pair

Does molecule H-bond with itself?

O/N atom w/ lone pair, O-H or N-H bond

Chair conformation energy (lowest to highest)

Chair, twist boat, boat, half chair

Types of gauche interactions

cis-1,2; trans-1,2-diequatorial

Meso checklist

even number of chiral carbons, constitutional symmetry, opposite R/S

Method for determining relationships

constitution, stereochem, conformation

Relative stability of resonance contributors

full octet, electronegativity, minimize charge separation

What is the hybridization state of a vinyl carbocation, carbon radical, and carbanion?

sp, sp, sp2

Gauche interactions

when large groups are 60 degrees apart

1,3-diaxials can be between what types of molecules?

two large molecules or one large molecule and H

How to identify cis/trans stereocenters

1,4 substituted cyclohexane or 1,3 substituted cyclobutane rings with 2 distinct groups

Assign R/S when lowest priority group is in the plane

Assign priority, swap #4 with dashed group, render configuration, reverse

what are conformational isomers

formed from rotation around single bonds

Reaction favors side with _____ pKa

higher

The most stable base is the _______ base, is the ________ acid

weakest, strongest