Write equations for the reaction of 1-butanol with each reagent. Where you predict no reaction, write NR. (a) Na metal (b) HBr, heat (c) HI, heat (d) PBr3 (e) SOCl2, pyridine (f) K2Cr2O7, H2SO4, H2O, heat (g) HIO4 (h) PCC (i) CH3SO2Cl, pyridine (j) CO2Cl2 and DMSO, followed by triethylamin (k) DMP (l) triethylamine

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ceruleanduck947Lv1

6 Oct 2020

Write equations for the reaction of 1-butanol with each reagent. Where you predict no reaction, write NR.

(a) Na metal

(b) HBr, heat

(c) HI, heat

(d) PBr₃

(e) SOCl₂, pyridine

(f) K₂Cr₂O₇, H₂SO₄, H₂O, heat

(g) HIO₄

(h) PCC

(i) CH₃SO₂Cl, pyridine

(j) CO₂Cl₂ and DMSO, followed by triethylamin

(k) DMP

(l) triethylamine

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From the choices provided below, list the reagent(s) in orderthat will react with 1-butanol to form butanoic acid. (Specify thereagents you would use to carry out the conversion by using lettersfrom the table. The reaction may require more than one step, if so,write the letters in the order that they are used, e.g., abc. Nomore than four steps are required for this synthesis. If two ormore ways of conversion to the same product are possible, show onlyone of them.)

Reagents available
a. Br2, CCl4	f. NaNH2 (3 equivalents)	k. NH3
b. HS?Na+, H2O	g. H2O	l. SOCl2, pyridine
c. H3PO4, heat	h. H2SO4, H2O	m. OsO4 / H2O2
d. Cl2 / H2O	i. HBr, heat	n. pyridinium chlorochromate (PCC)
e. K2Cr2O7, H2SO4, H2O, heat	j. RCO3H

List the letter that corresponds to the reagent from the reagenttable you need to carry out the following synthesis in 5 steps orless.
Heat may not appear on the reagent table with the reagent, but youcan assume you have a hot plate and can supply neededheat.
There may be more boxes than you need. Type NA in the blank of any extra box(es).

2-ethylbut-1-ene %u2192 2-ethyl-2-methylbutanoic acid

step 1
step 2
step 3
step 4
step 5

Reagents:

A: HCl, 25o

B: Cl2, h%u03BD

C: Br2, h%u03BD, heat

O: SOCl2, pyridine

E: PBr3

X: conc. H2SO4, heat

G: KOC(CH3)3, HOC(CH3)3, heat

EE: H2, Pd

(other metals: Ni, Rh, Pt)

I: HCl, 0oC

J: 50% H2SO4, H2O

M: HBr, 0oC

F: HBr, peroxides or HBr, h%u03BD

RR: 1. B2H6, diglyme 2. H2O2, NaOH or 1. BH3-THF 2.H2O2, NaOH

P: Cl2 or Br2, CHCl3 or CCl4, dark, cool

Q: Cl2 or Br2, H2O

N: peroxyacetic acid

S: 1. O3 2. H2O, Zn or 1. O3 2. HOCH3(CH3)2S

PP: 1. O3 2. H2O

U: KOCH2CH3 HOCH2CH3

V: NaNH2, NH3

GG: 1. 3NaNH2, NH3 2. H2O

HH: H2, Lindlar

II: Na, NH3

QQ: H2SO4, HgSO4

R: NBS, benzoyl peroxide, CCl4, heat

SS: Na, NH3, HOCH3

BB: Na2Cr2O7, H2O, H2SO4, heat

NN: HNO3, H2SO4

OO: Br2, FeBr3 or Cl2, FeCl3

Z: AlCl3

Y: Zn(Hg), HCl

D: H2NNH2, KOH, triethylene glycol, heat

AA: PCC, CH2Cl2 or PDC, CH2Cl2

TT: Mg

CC: Na

DD: OsO4 (cat) (CH3)3COOH,tert-butyl alcohol,NaOH

JJ: HIO4

KK: LiAlH4

LL: NaBH4

H: NaOH, heat MM: ethylene oxide

K: NaCN

L: NaOH

T: aqueous acid

W: CO2

FF: SOCl2

Specify the reagent you would use in step of the following synthesis:

a. LiAIH4
b. H2SO4
c. HCl
d. HBr
e. SOCl2
f. PBr3
g. pyridinium chlorocgromate (PCC)
h. NaH
i. NaOH
j. CH3MgBr
k. CH3CH2MgBr
l. C6H5MgBr (phenylmagnesium bromide)
m. (CH3)2CHMgBr
n. CrO3