Exam 4 Important reactions

Question 1

H2 w/ Pd-C and Alkene

Answer 1

• H adds to each DB carbon

- SYN

Question 2

CrO3 and H2SO4 and alcohol

Answer 2

• Primary carbons turns into carboxylic acid
• Secondary carbons turns into ketone
• Tertiary carbons stay ketone

Question 3

X2 and H2O and Alkene

Answer 3

• OH adds to more sub. carbon
• X adds to less sub. carbon
• ANTI

Question 4

BH3 and H2O2, KOH Alkynes

Answer 4

• Forms ALDEHYDE on least substituted carbon
• TB -> SB
• TAUTOMERIZATION

Question 5

OSO4 and NaHSO3 and Alkenes

Answer 5

• 2 OH’s add to each DB carbon

- SYN

Question 6

PCC and alcohol

Answer 6

• similar to CrO3 but it doesn’t oxidize past aldehyde & ketone

Question 7

O3 and Alkene

Answer 7

• DB breaks and it forms 2 pdts w/ C=O where the DB was

- Makes Ketone or aldehyde

Question 8

LAH and H2O and Tosylate

Answer 8

• Removes tosylate (OTs) and adds H

Question 9

MCPBA (or PCC) and Alkenes

Answer 9

• Makes epoxide @ DB

- Keep stereochem

Question 10

Na, NH3 or Li, NH3 and Alkynes

Answer 10

• TB -> DB
• Adds 1 H on each carbon
• ANTI (trans-alkene)

Question 11

H-X and Alkene

Answer 11

• Markovnikov = X adds on more substituted carbon
• SYN or ANTI
• C+ arrangement

Question 12

X2 and Alkynes

Answer 12

• X2 adds to carbons on both sides of TB
• TB -> SB
• ANTI

Question 13

X2 and Alkene

Answer 13

• X adds to both sides of DB

- ANTI

Question 14

H2 and Pd-C and alkyne

Answer 14

• TB -> SB
• Replaces TB w/ 2 H’s on both carbons
• SYN

Question 15

H-X and Alkynes

Answer 15

• TB -> SB
• Markovnikov = 2 X’s add to most sub carbon
• C+ rearrangement

Question 16

LAH and H2O and X

Answer 16

• Very basic

- Removes LG (X) adds an H

Question 17

H2O and H2SO4 and Alkynes

Answer 17

• Markovnikov = OH adds to more sub. carbon and H to the other
• TAUTOMERIZATION
• Forms KETONE on more substituted carbon

Question 18

H2 and lindlar’s catalyst and alkyne

Answer 18

• TB -> DB ONLY!
• 1 H on each carbon
• SYN (cis-alkene)

Question 19

BH3 and H2O2, KOH and Alkene

Answer 19

• Oxidation addition of H and OH
• Anti-Markovnikov = OH adds to least substituted carbon
• SYN

Question 20

Alkylation of Acetylide Ion

Answer 20

• Uses NaNH2 and C-X

- Makes reactant an anion to bond w C-X

Question 21

H2O and H2SO4 (H3O+) and Alkene

Answer 21

• Addition of H and OH
• Markovnikov = OH adds to more substituted side
• SYN and ANTI
• C+ rearrangement

Question 22

O3 and Alkynes

Answer 22

• Makes carboxylic acids

- If terminal, CO2 will also form

Question 23

LAH and H2O and epodixes

Answer 23

• Since LiAlH4 is very basic, it breaks the epoxide ring @ LEAST substituted side
• ANTI