ORG CHEM CONNECT CARD
6th Edition
ISBN: 9781264860746
Author: SMITH
Publisher: MCG
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Chapter 13, Problem 34P
Interpretation Introduction
Interpretation: The structures of
Concept introduction: Monochlorination is a radical substitution reaction. In this reaction,
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Five isomeric alkanes (A–E) having the molecular formula C6H14 are each treated with Cl2 + hv to give alkyl halides having molecular formulaC6H13Cl. A yields five constitutional isomers. B yields four constitutionalisomers. C yields two constitutional isomers. D yields threeconstitutional isomers, two of which possess stereogenic centers. Eyields three constitutional isomers, only one of which possesses astereogenic center. Identify the structures of A–E.
Treatment of a hydrocarbon A (molecular formula C9H18) with Br2 in the presence of light forms alkyl halides B and C, both having molecular formula C9H17Br. Reaction of either B or C with KOC(CH3)3 forms compound D (C9H16) as the major product. Ozonolysis of D forms cyclohexanone and acetone. Identify the structures of A–D.
Draw a structural formula for the major organic product of the following reaction:
CH3
CH3
●
CH3
CH3
AAVIL
+
Br₂
Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring.
• Do not show stereochemistry in other cases.
●
If enantiomers are formed, just draw one.
CH₂Cl₂
Sn [F
?
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Chapter 13 Solutions
ORG CHEM CONNECT CARD
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - Prob. 4PCh. 13.3 - Prob. 5PCh. 13.4 - Prob. 7PCh. 13.5 - Problem 15.8 Which bond in the each compound is...Ch. 13.6 - Prob. 9PCh. 13.6 - Prob. 10PCh. 13.7 - Prob. 11P
Ch. 13.7 - Prob. 12PCh. 13.8 - Prob. 13PCh. 13.8 - Prob. 14PCh. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 34PCh. 13 - 15.37 What alkane is needed to make each alkyl...Ch. 13 - 15.38 Which alkyl halides can be prepared in good...Ch. 13 - Prob. 37PCh. 13 - 15.40 Explain why radical bromination of p-xylene...Ch. 13 - a. What product(s) (excluding stereoisomers) are...Ch. 13 - Prob. 40PCh. 13 - 15.43 Draw the products formed when each alkene is...Ch. 13 - 15.44 Draw all constitutional isomers formed when...Ch. 13 - 15.45 Draw the organic products formed in each...Ch. 13 - Prob. 45PCh. 13 - 15.47 Treatment of a hydrocarbon A (molecular...Ch. 13 - 15.48 Draw the products formed in each reaction...Ch. 13 - 15.53 Consider the following bromination: .
a....Ch. 13 - 15.54 Draw a stepwise mechanism for the following...Ch. 13 - Prob. 57PCh. 13 - 15.57 Devise a synthesis of each compound from...Ch. 13 - Prob. 59PCh. 13 - Prob. 60PCh. 13 - 15.60 Devise a synthesis of each compound using ...Ch. 13 - Prob. 62PCh. 13 - Prob. 63PCh. 13 - 15.63 As described in Section 9.16, the...Ch. 13 - 15.64 Ethers are oxidized with to form...
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