associate the reagents and reactions

Question 1

+HX

Answer 1

adding an H and a 7A on an alkene

Question 2

X2 in CH2CL2

Answer 2

adding a Br on opposite sides of an alkene

Question 3

X2 in H2O/alcohol

Answer 3

adding an OH and a Br on opposite sides of an alkene (major product)

Question 4

H2O in acid

Answer 4

alkene -> markovnicov alcohol

Question 5

i) Hg(OCOCH3)2 in THF
ii)NaBH4 in OH-

Answer 5

alkene -> markovnicov alcohol
*if unstable intermediate (e.g. carbocation rearrangement)

Question 6

i) BH3 in THF
ii) H2O2 in OH-

Answer 6

alkene -> non-markovnicov alcohol

Question 7

+H2 (3 atm) with Pd catalyst

Answer 7

adding 1 or 2 H on a double or triple bond to get an alkane
alkene -> alkane
alkyne -> alkane

reduce an acyl substituent on a ring

Question 8

+H2 (3 atm) with Lindlar catalyst

Answer 8

alkyne -> cis alkene

Question 9

+RCO3H in CH2Cl2

Answer 9

akene -> epoxide

Question 10

i) O3
ii) Zn in weak acid or H2O2 in acid

Answer 10

alkene -> carbonyl

Question 11

i) OsO4
ii) NaHSO3 in water

Answer 11

alkene -> cis glycol

Question 12

epoxide + H3O+

Answer 12

trans glycol

Question 13

Na in cold NH3

Answer 13

alkyne -> trans-alkene

Question 14

NaNH2 in liquid NH3

Answer 14

chain elongation for alkynes

Question 15

Br2 (or Cl2) in FeBr3 (or FeCl3)

Answer 15

adding Br or Cl on a benzene

Question 16

HNO3 in H2SO4

Answer 16

benzene -> nitrobenzene (benzene with NO2)

Question 17

i) Fe, H3O+ (or H2 in Pd)
ii) OH-

Answer 17

benzene -> aniline (benzene with NH2)

Question 18

+SO3 in H2SO4

Answer 18

benzene -> benzenesulfonic acid (benzene with SO3H)

Question 19

i) cold NaOH
ii) hot NaOH
iii) H3O+

Answer 19

benzenesulfonic acid -> phenol

Question 20

+R-Cl with AlCl3

Answer 20

Friedel-Crafts alkylation
(addition of alkyl group on benzene)

Question 21

+RCOCl with AlCl3

Answer 21

Friedel-Crafts acylation
(addition of acyl group on aromatic ring)

Question 22

+KMnO4 in H2O

Answer 22

oxydation of an alkyl substituent on a ring to a carboxylic acid

Question 23

What is the Grignard reagent?

Answer 23

An organometallic compound where the carbon bears a partial negative charge (good nucleophile + reacts with weak acids)

Question 24

i) Mg in THF

Answer 24

add Mg to R-Br
gives Grignard reagent

Question 25

+NaBH4 in water

Answer 25

aldehyde -> 1°alcohol
ketone -> 2° alcohol

Question 26

+LiAlH4 in ether followed by H3O+

Answer 26

carboxylic acid -> 1° alcohol
ester -> 2x 1° alcohol

Question 27

+ Grignard reagent in ether followed by H3O+

Answer 27

Formaldehyde -> 1° alcohol
Aldehyde -> 2° alcohol
Ketone -> 3° alcohol

Question 28

Alcohol + active metal (1A group) = ?

Answer 28

alkoxide ion (strong not aqueous base) + H2

Question 29

How to convert 3° water soluble alcohol to alkyl halide?

Answer 29

+HCl through Sn1

Question 30

How to convert 3° non water soluble alcohol to alkyl halide?

Answer 30

+HX (0° in ether) through Sn1

Question 31

+SOCl2 in organic base (e.g. pyridine)

Answer 31

1°/2° alcohol -> R-Cl

Question 32

+PCl3 (or PBr3)

Answer 32

1°/2° alcohol -> R-Cl (or R-Br)

Question 33

+H3PO4 or H2SO4 with heat

Answer 33

alcohol -> alkene
(acid catalyzed dehydration)

Question 34

+CrO3 with water and sulphuric acid (Jones)

Answer 34

1° alcohol -> carboxylic acid
2° alcohol -> ketone

Question 35

+CrO3 with HCl and pyridine

Answer 35

1° alcohol -> aldehyde
2° alcohol -> ketone

Question 36

+ Dess-martin periodinane

Answer 36

1° alcohol -> aldehyde
2° alcohol -> ketone

Question 37

+(KSO3)2NO in H2O

Answer 37

1° alcohol -> carboxylic acid
2° alcohol -> ketone

Question 38

+ NaH in THF followed by reaction with an alkyl halide

Answer 38

alcohol -> non-symmetrical ether

Question 39

How to make a symmetrical ether from a 1° alcohol?

Answer 39

Through Sn2