Organic Chemistry 2 Test 1

What is the pKa of HCl?
-8
What is the pKa of H3O+?
-2
What is the pKa of NH4+?
+9
What is the pKa of NH3?
+35
What is the pKa of H2O?
+16

What is the pKa of -*ROH?

 

 

 

*Note: “R” is a generic representation for various alkyl groups. The bulk of the alkyl group can impact acidity, but for a ballpark pKa value, this works.

+16
What is the pKa of -RCOOH?
+5
What is the pKa of phenol?
+10
What is the pKa of p-toluene sulfonic acid?
-3
What is the pKa of -RCOCH2COR-?
+10
What is the pKa of -RCOCH3?
+20
What is the pKa of HCCH?
+25
What is the pKa of H2CCH2?
+44
What is the pKa of CH4?
+50
If you have nitrobenzene, which reaction would you use to make aniline?

Use Zn(Hg) and HCl or

Fe and HCl or

Ni and H2 or

Sn and HCl

If you have aniline, which reaction would you use to make nitrobenzene?
CF3COOH
If you have a COR- group on a benzene ring, how do you make that group into CH2R-?

Zn(Hg) and HCl or

NH2NH2 and OH

If you have a CH2R group on a benzene ring, how do you make that group into COR-?
CrO3, H2SO4, H2O and heat
If you have SO3H on a benzene ring, how do you get benzene?
H2O, cat. H2SO4 and heat
If you have aniline, how do you make the NH2 group into HNCOCH3?
H3CCOCl and pyridine
How do you remove the -COCH3 group from -NH on a benzene ring to get aniline?
NaOH and H2O
How do you make a OCOCH3 group on a benzene ring starting from phenol?
H3CCOCl and pyridine
How do you remove a H3CCOO group from a benzene ring to get phenol?
NaOH and H2O
How do you get anisole from phenol?
NaOH and CH3I
How do you get phenol from anisole?
With concentrated HI
How do you prepare an acid chloride (-RCOCl) from a carboxylic acid (-RCOOH)?
With SOCl2
Describe the halogens (I, Br, Cl, F) in terms of activating/deactivating, EWG/EDG, and directing effects.
The halogens are weak deactivators, weak EWGs, and o and p directors.
Describe carbonyl groups (-C=OR) in terms of activating/deactivating, EWG/EDG, and directing effects.
The carbonyl groups are moderate deactivators, moderate EWGs, and meta directors.
Describe -CN, -SO3H, -NH3, -NH2R, -NHR2, -NR3, -CF3, -OH2, and -NO2 in terms of activating/deactivating, EWG/EDG, and directing effects.
These are all strong deactivators, strong EWGs, and meta directors.
Describe -NH2, -NHR, -NR2, -OH, and -OR in terms of activating/deactivating, EWG/EDG, and directing effects.
These are all strong activators, strong EDGs, and o and p directors.
Describe alkyl, phenyl, and vinyl groups in terms of activating/deactivating, EWG/EDG, and directing effects.
These are all weak activators, weak EDGs, and o and p directors.
Describe -NHCOR and -OCOR in terms of activating/deactivating, EWG/EDG, and directing effects.
These are moderate activators, moderate EDGs, and o and p directors.
What is the Lindlar catalyst and what does it do?

Pd-CaCO3, Pb(OAc)2, and quinoline

 

 It hydrogenates alkynes to cis alkenes.

How do you hydrogenate an alkyne to a trans alkene?
Use sodium metal (Na0) and liquid ammonia (NH3(l)).
What are the reagents involved in mercury ion catalyzed hydration of an alkyne?
H2SO4, H2O, and HgSO4
In mercury ion catalyzed hydration of alkynes, does the H2O add to the alkyne according to Markovnikov’s rule?
Yes. The O adds to the most highly substituted C.
Which reagents are used in anti-Markovnikov hydration of alkynes?

1) BHR2

2) H2O2 and OH

What do we use NBS for?
Adding a single Br to an alkene, as opposed to creating a viinal dihalide, as occurs with excess Br. NBS keeps the concentration of Br very low. Br will add wherever a radical can form (on allyic Hs).
Do organolithium reagents (R-Li) add 1,2, 1,4, or both to enones?
1,2
Does LiAlH4 add 1,2, 1,4, or both to enones?
1,2
Does NaBH4 add 1,2, 1,4, or both to enones?
1,2
Do grignard reagents (RMgX) add 1,2, 1,4, or both to enones?
both 1,2 and 1,4
Name 3 methods for forming an enone.

1) Aldol condensation

2) Mono alpha-halogenate (acidic conditions), followed up by basic E2 H-X elimination

3) Oxidation of an allylic alcohol using MnO2

Do organo cuprates (R2CuLi) add 1,2, 1,4, or both to enones?
1,4
Does RMgBr + copper salts add 1,2, 1,4, or both to enones?
1,4
Do enolates add 1,2, 1,4, or both to enones?
1,4 (net)
Does hydroxide (OH-) add 1,2, 1,4, or both to enones?
1,4 (net)
Do alkoxides (OR-) add 1,2, 1,4, or both to enones?
1,4 (net)
Do amines add 1,2, 1,4, or both to enones?
1,4 (net)
What do you get when you add H3PO2 to an arenediazonium ion?
Benzene
What do you get when you add H2O to an arenediazonium ion?
Phenol
What do you get when you add CuBr to an arenediazonium ion?
Bromobenzene
What do you get when you add CuCl to an arenediazonium ion?
Chlorobenzene
What do you get when you add CuCN to an arenediazonium ion?
A nitrile group on a benzene ring (C triple bond N substituent)
What do you get when you add HBF4 to an arenediazonium ion?
Fluorobenzene
What do you get when you add KI to an arenediazonium ion?
Iodobenzene
x

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