Exam 3 Sebahar

Question 1

What is important to remember about E2?

Answer 1

Anti peri planar arrangement of H and X

Question 2

Alkene + McPBA?

Answer 2

Epoxide

Question 3

Alcohol + H2SO4 or H30+ and Heat

Answer 3

Alkene

Question 4

Alcohol + POCl3, py

Answer 4

Alkene (E2)

Question 5

Alcohol + HX

Answer 5

RX + H2O, protonate the alcohol, creates a leaving group and then water comes in.

Question 6

Alcohol + SOCl2, py

Answer 6

R-Cl with inversion of stereochemistry

Question 7

Alcohol + PBr3

Answer 7

R-Br with Inversion of Stereochemistry

Question 8

Alcohol + TsCl, py

Answer 8

R-OTs with retention of stereochemistry

Question 9

R-O-R + HX (2 equivalents)

Answer 9

R-X + R-X + H2O (Cleavage)

Question 10

Epoxide + Nucleophile (basic conditions)

Answer 10

Nucleophile attacks the less substituted side

Question 11

Epoxide + Acidic Conditions

Answer 11

Z (conjugate base) attacks the more substituted side

Question 12

Alkene + HX

Answer 12

H bonds to less substituted carbon, syn and anti

Question 13

Alkene + H2SO4, H2O

Answer 13

H bonds to less substituted carbon, syn and anti addition

Question 14

Alkene + H2SO4, HOR

Answer 14

H bonds to the less substituted carbon, syn and anti addition, OR on one side instead of OH

Question 15

Alkene + X2

Answer 15

Anti Addition

Question 16

Alkene + X2, H2O

Answer 16

X bonds to the less substituted Carbon, anti addition occurs

Question 17

Alkene + BH3 or 9BBN, H2O2, -OH

Answer 17

OH bonds to the less substituted carbon, syn addition only

Question 18

Alkyne + HX (2 equivalents)

Answer 18

The halogens bond to the same carbon and the hydrogens bond to the same carbon.

Question 19

Alkyne + X2 (2 equivalents)

Answer 19

halogens bond and saturate both carbons. Bridged halonium ions formed as intermediates

Question 20

Alkyne + H2O, H2SO4, HgSO4

Answer 20

ENOL which changes into a KETONE

Question 21

Alkyne + BH3, H2O2, -OH

Answer 21

ENOL to an ALDEHYDE

Question 22

Alkene + H2, Pd/C or other Metal/C

Answer 22

Alkane

Question 23

Alkyne + 2 H2, Pd/C

Answer 23

Alkane

Question 24

Alkyne + H2, Lindlar’s Catalyst

Answer 24

Cis Alkene, syn addition

Question 25

Alkyne + Na, NH3

Answer 25

Trans Alkene , anti addition

Question 26

IR Aromatic Ring

Answer 26

Two peaks, 1500 and 1600

Question 27

Alkene

Answer 27

1650

Question 28

Carbonyl

Answer 28

1700

Question 29

Alkyne

Answer 29

2100

Question 30

Alkane

Answer 30

2900

Question 31

Terminal Alkyne

Answer 31

3300

Question 32

Carboxylic Acid O-H

Answer 32

2400-3000, very broad and irregular

Question 33

Alcohol, amine, amide IR

Answer 33

3200-3400 Broad, regular

Question 34

Alcohol NMR

Answer 34

Between 2-5 but broad

Question 35

Aromatic Ring NMR

Answer 35

7

Question 36

Amide NMR

Answer 36

10

Question 37

Aldehyde and Carboxylic Acid NMR

Answer 37

11

Question 38

KOt-Bu

Answer 38

E2. It will grab the least substituted Hydrogen

Question 39

R-X (alkyl halide) + LAH, H20

Answer 39

R-H (Alkane)

Question 40

Epoxide + LAH, H20

Answer 40

Alcohol. SN2 mechanism, LAH attacks the less substituted side.

Question 41

Alkene + 1. RCO3H, 2. H2O

Answer 41

1,2 diol. Epoxide ring intermediate, Anti addition

Question 42

Alkene + 1. OsO4, 2. NaHSO3, H2O or 1. OsO4, NMO, 2. NaHSO3, H20 or KMnO4, H2O, -OH

Answer 42

1,2 diol. Syn addition

Question 43

Alkene + 1. O3 2. Zn, H2O, CH3SCH3

Answer 43

Ketone + Aldehyde Ketone + Ketone Aldehyde + Aldehyde

Question 44

Internal Alkyne + 1. O3, 2. H20

Answer 44

cleaves into 2 Carboxylic acids

Question 45

Terminal Alkyne + 1. O3, H2O

Answer 45

Cleaves into 1 Carboxylic acid and CO2

Question 46

Primary Alcohol + PCC

Answer 46

Aldehyde

Question 47

Primary Alcohol + CrO3, H2SO4, H20

Answer 47

Carboxylic Acid

Question 48

Secondary Alcohol + PCC or CrO3

Answer 48

Ketone

Question 49

Alkene + 1. O3, 2. H2O2, NaOH, H2O

Answer 49

Carboxylic Acid (replace H with OH) and Ketone