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Chapter 9: Q22P (page 486)

Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamyl groups. Disiamylborane is prepared by the reaction of BH3. THF with an alkene.

(a) Draw the structural formulas of the reagents and the products in the preparation of disiamylborane.

(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why is Sia3B not formed?

Short Answer

Expert verified

(a)

(b) Sia3B is not formed due to steric hindrance already present in Disiamylborane.

Step by step solution

01

Preparation of Disiamyl borane

Disiamylborane is prepared by reacting alkene 2-methyl-2-butene with borane (BH3).

02

Reason why Sia3B was not formed

Disiamylborane (Sia2BH) is already too sterically hindered to add the third B-H across another alkene. Thus, the reaction goes only far as dialkylborane (Sia2BH) and is not formed.

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Most popular questions from this chapter

Question: Predict the products formed when CH3CH2-C鈮�C:Na+ reacts with the following compounds.

(a)ethyl bromide

(b)tert-butyl bromide

(c)formaldehyde

(d)cyclohexanone

(e)CH3CH2CH2CHO

(f)cyclohexanol

(g)butan-2-one,CH3CH2COCH3

(a)Count the elements of unsaturation in cicutoxin, capillin, and panaxytriol.

(b) Draw structural formulas of at least two alkynes of each molecular formula.

(1) C5H8 (2) C8H10 (3) C9H12

Deduce the structure of each compound from the information given. All unknown in this problem have molecular formula C8H12.

(a)Upon catalytic hydrogenation, unknown Wgives cyclooctane. Ozonolysis of W,followed by reduction with dimethylsulfide, gives octanedioic acid,HOOC-(CH2) 6-COOH . Draw the structure of W.

(b)Upon catalytic hydrogenation, unknown Xgives cyclooctane. Ozonolysis of X,followed by reduction with dimethyl sulfide, gives two equivalents of butanedial , O =CH -CH2 CH 2-CH = O. Draw the structure of X.

(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.

(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO ) group on C1 and a one-carbon aldehyde (CHO) group on C2. Draw the structure of Z.

Question: Give IUPAC names for the following compounds.

a.

b.

c.

d.

e.

f.

Give common names for the following compounds.

(a)CH3鈭�C鈮�C鈭�CH2鈭�CH3 (b)Ph鈭�C鈮�C鈭�H

(c) 3-methyloct-4-yne (d)(CH3)3C鈭�C鈮�C鈭�CH(CH3)CH2鈭�CH3
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