10 ch06

Download Document
Showing pages : 1 - 5 of 17
This preview has blurred sections. Sign up to view the full version! View Full Document
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 184 CHAPTER 6 The Reactions of Alkynes An Introduction to Multistep Synthesis Important Terms acetylide ion the conjugate base of a terminal alkyne RC C aldehyde a compound with a carbonyl group that is bonded to an alkyl group and to a hydrogen (or bonded to two hydrogens). O C R H or O C H H alkylation reaction a reaction that adds an alkyl group to a reactant. alkyne a hydrocarbon that contains a triple bond. carbonyl group a carbon doubly bonded to an oxygen. O C enol an α , β-unsaturated alcohol. OH C geminal dihalide a compound with two halogen atoms bonded to the same carbon. internal alkyne an alkyne with its triple bond not at the end of the carbon chain. keto-enol tautomers a ketone and its isomeric α , β-unsaturated alcohol. O CR RCH 2 keto enol RCH CR OH ketone a compound with a carbonyl group that is bonded to two alkyl groups. O C R R π-complex a complex formed between an electrophile and a triple bond. polymer a large molecule made by linking up many small molecules called monomers. radical anion a species with a negative charge and an unpaired electron. Chapter 6 185 retrosynthetic analysis working backward (on paper) from a target molecule to available starting or materials. retrosynthesis tautomerization interconversion of tautomers. tautomers isomers that are in rapid equilibrium. The keto and enol tautomers differ in the location of a double bond and a hydrogen. terminal alkyne an alkyne with its triple bond at the end of the carbon chain. vinylic cation a compound with a positive charge on a vinylic carbon. vinylic radical a compound with an unpaired electron on a vinylic carbon. 186 Chapter 6 Solutions to Problems 1. The molecular formula of a noncyclic hydrocarbon with 14 carbons and no π bonds is 14 30 2 +2 C H (C H ) n n . Because a compound has two fewer hydrogens for every ring and π bond, a compound with one ring and 4 π bonds (2 triple bonds) would have 10 fewer hydrogens than the 2 +2 C H n n formula. Thus, the molecular formula is 14 20 C H . 2. a. 2 2 2 3 ClCH CH C CCH CH c. CH 3 CHC CH 3 CH e. HC CCH 2 CCH 3 CH 3 CH 3 b. d. 2 HC CCH Cl f. 3 3 CH C CCH 3. To answer this question, you need to have the information in Section 6.2. a. 1-bromo-1,3-pentadiene b. 1-hepten-5-yne c. 4-hepten-1-yne 4. HC CCH 2 CH 2 CH 2 CH 3 CH 3 C CCH 2 CH 2 CH 3 CH 3 CH 2 C CCH 2 CH 3 1-hexyne butylacetylene 2-hexyne methylpropylacetylene 3-hexyne diethylacetylene CH 3 CH 2 CHC CH CH 3 CHCH 2 C CH CH 3 CHC CCH 3 3-methyl-1-pentyne sec-butylacetylene 4-methyl-1-pentyne isobutylacetylene CH 3 CH 3 CH 3 4-methyl-2-pentyne isopropylmethylacetylene CH 3 CC 3,3-dimethyl-1-butyne tert-butylacetylene CH CH 3 CH 3 5. a. 5-bromo-2-pentyne c. 1-methoxy-2-pentyne b. 6-bromo-2-chloro-4-octyne d. 3-ethyl-1-hexyne 6. a. 1-hepten-4-yne d. 3-butyn-1-ol b. 4-methyl-1,4-hexadiene e. 1,3,5-heptatriene c. 5-vinyl-5-octen-1-yne f. 2,4-dimethyl-4-hexen-1-ol 7. pentane 1-pentene 1-pentyne Chapter 6 187 ...
View Full Document