Org.chem problem from the KAPLAN~

[ippie]

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The problems from the Kaplan.
I think the solution is wrong. What do you guys think about?


DAT Nomenclature & Functional Groups Quiz - problem 4.
CH3CH2CH2CH(CH3)CHCH(CH3)2CH(CH3)CH2CH3
Nomenclature is 4-isopropyl-3,5-dimethyloctane, but the solution says 3,5-dimethyl-4-isopropyloctane. Which is right?

DAT Nomenclature & Functional Groups Quiz - problem 10.
(CH3)2C(CH2CH3)CH2CHClCH3
Nomenclature is 2-chloro-4,4-dimethylhexane, but the solution says 5-chloro-3,3-dimethylhexane. Which is right?

DAT Addition and Elimination Quiz - problem 9.
I understand everyting in the solution except the last sentence "2-pentanol can dehydrate to from 2-pentene, which can then react with HBr to form 3-bromo-pentane."
I think the last sentence should be corrected like "2-pentanol can dehydrate to from 2-pentene, which canthen react with HBr to form 3-bromo-pentane & 2-bromo-pentane." Right?

DAT Spectroscopy Quiz - problem 4.
Which or the following is not a plausible result of applying NMR to an organic compound?
A. Four singlets
B. Two triplets
C.A doublet
D. A singlet
The answer is C, but i don't understand why.

 

[armorshell]

The problems from the Kaplan.
I think the solution is wrong. What do you guys think about?


DAT Nomenclature & Functional Groups Quiz - problem 4.
CH3CH2CH2CH(CH3)CHCH(CH3)2CH(CH3)CH2CH3
Nomenclature is 4-isopropyl-3,5-dimethyloctane, but the solution says 3,5-dimethyl-4-isopropyloctane. Which is right?

DAT Nomenclature & Functional Groups Quiz - problem 10.
(CH3)2C(CH2CH3)CH2CHClCH3
Nomenclature is 2-chloro-4,4-dimethylhexane, but the solution says 5-chloro-3,3-dimethylhexane. Which is right?

DAT Additin and Elimination Quiz - problem 9.
I understand everyting in the solution except the last sentence "2-pentanol can dehydrate to from 2-pentene, which canthen react with HBr to form 3-bromo-pentane."
I think the last sentence should be corrected like "2-pentanol can dehydrate to from 2-pentene, which canthen react with HBr to form 3-bromo-pentane & 2-bromo-pentane." Right?

DAT Spectroscopy Quiz - problem 4.
Which or the following is not a plausible result of applying NMR to an organic compound?
A. Four singlets
B. Two triplets
C.A doublet
D. A singlet
The answer is C, but i don't understand why.

A. You are right

B. You are right

C. You're reading too much into the problem. 2-pentene can react with HBR to form 3-bromopentane. It can also react to form 2-bromopentene but that's irrelevant to the problem.

D. The reason C is the answer is because an H-NMR with a single doublet makes no sense, if there was an additional proton adjacent to the proton registering a doublet, it also would register a signal.